Cyclohexane Derivative

1. Field of the Invention

This invention relates to a cyclohexane derivative useful as a liquid crystal material. More particularly, it relates to a liquid crystalline compound having an alkenyl group at the end of its molecule and a liquid crystal composition containing the compound.

2. Description of the Related Art

Display elements utilizing liquid crystals have been broadly used for watches, electronic calculators, etc. These liquid crystal display elements are those utilizing the optical anisotropy and the dielectric anisotropy of liquid crystal substances. Liquid crystal phases include nematic liquid crystal phase, smectic liquid crystal phase and cholesteric liquid crystal phase, and among the above phases liquid crystal display elements utilizing nematic liquid crystal phase have been most broadly and practically used. Such display elements include those of TN (twisted nematic) mode, DS (dynamic scattering) mode, guest-host mode, DAP mode, etc., corresponding to the electro-optic effect applied to liquid crystal display, and as the liquid crystal substances utilized for the respective display elements, those exhibiting liquid crystal phases within a temperature range as broad as possible in the natural state are preferred. A large number of liquid crystal compounds have already been known, but at present, there is no single liquid crystal substance satisfying such conditions, but several kinds of liquid crystal substances or non-liquid crystal compounds have been mixed to be practically used. These substances are required to be stable to moisture, light, heat, air, etc. In particular, recently, there has been an increasing importance of substances having a low optical anisotropy, as a material for liquid crystal display element for active matrix mode represented by thin film transistor (TFT) mode. Further, it has been required for the liquid crystal material that its compatibility with a number of already existing liquid crystal materials is as large as possible at low temperatures.

The following compounds have so far been known as compounds similar to those of the present invention: ##STR2##

These compounds, particularly (I), (II), (III), (VI) and (VII), have been reported to have a large dielectric anisotropy value (.DELTA..epsilon.) and a low viscosity and exhibit an effect of lowering the threshold voltage without raising the viscosity. However, according to research of the present inventors, it has been found that the .DELTA..epsilon. value is comparatively small and the threshold voltage cannot be sufficiently lowered.

The object of the present invention is to provide a cyclohexane derivative as a liquid crystal compound which has a low viscosity and can sufficiently lower the threshold voltage.

The present inventors have conducted extensive research in order to solve the above mentioned problems, and as a result, have found a compound having a novel structure and having improved characteristics over known liquid crystal compounds, and have completed the present invention.

The cyclohexane derivative of the present invention is a cyclohexane derivative expressed by the formula (I) ##STR3## wherein X represents a fluorine atom, a trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, --A-- represents 1,4-cyclohexylene or 1,4-phenylene, --B-- represents 1,4-cyclohexylene, 1 represents 0, 1 or 2, m represents 0, 1 or 2, and l+m.gtoreq.1, Z represents --CH.sub.2 CH.sub.2 -- or a single bond, n represents an integer of 0 to 4, R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms, and when R represents an alkyl group, the double bond has a trans-configuration, and a liquid crystalline mixture containing at least one of the cyclohexane derivatives.

Compounds having an alkenyl substituent group, so (far reported, have a higher elastic constant ratio (K.sub.33 /K.sub.11) than those of compounds having a normal alkyl substituent group, as reported in various papers, and hence they are suitable as a liquid crystal material for STN display elements.

The characteristic of the liquid crystal compound provided by the present invention, surprisingly enough, is that it has a lower elastic constant ratio (K.sub.33 /K.sub.11) than those of compounds having a normal alkyl substituent group, in spite of having an alkenyl substituent group. Materials having a low K.sub.33 /K.sub.11 are steep in the electro-optic characteristic of TN mode, and exhibit a superior multiplex characteristic.

This fact is known for example by the following articles:

a) J. Nehring, advance in Liquid Crystal Research and Applications (ed. L. Bata)., P1155. Pergamon Press

b) G. Baur, The Physics and Chemistry of Liquid Crystal Devices (ed. G. J. Sprokel)., P61, Plenum (1980 ).

c) Y. Takahashi, T. Uchida and M. Wada, Mol. Cryst. Liq. Cryst., 66, 171 (1981).

Further, since the compound of the present invention is chemically stable, it is possible to prepare a composition having a superior multiplex characteristic and capable of effecting a low voltage drive by using the compound of the present invention.

As the compound of the formula (I), compounds expressed by the formulas Ia to Ie can be exemplified (the definitions of the respective symbols are the same as those in the formula (I)). ##STR4##

Particularly preferable compound among those of the respective formulas will be illustrated below. ##STR5##

Compounds of the formula (I) wherein R represents an alkyl group, form a trans-configuration in the aspect of the steric structure directed to the double bond having R bonded thereto. The alkyl group of R is preferably a linear alkyl group of 1 to 7 carbon atoms, more preferably a methyl group, ethyl group, propyl group, butyl group and pentyl group.

The liquid crystal composition provided by the present invention is a liquid crystal dielectric comprising a component (A) containing at least one of the compounds expressed by the formula (I) and further, a component (B) containing at least one of compounds having a high dielectric anisotropy of preferably .DELTA..epsilon..gtoreq.5, a component (C) containing at least one of compounds having a low dielectric anisotropy of .vertline..DELTA..epsilon..vertline.<5 and a component (D) containing at least one of compounds having a clearing point exceeding 80.degree. C., and further, if required, another component (E).

Compounds particularly preferred as the component (B) will be shown below. ##STR6##

In tile above formulas, R represents an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two non-adjacent carbon atoms of the groups may be replaced by an oxygen atom.

Compounds particularly preferred as tile component (C) will be shown below. ##STR7##

In these formulas, R and R' each represent an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two non-adjacent carbon atoms of the groups may be replaced by an oxygen atom. Particularly preferable compounds as the component (D) are shown below. ##STR8##

In these compounds, R and R' each represent an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two non-adjacent carbon atoms of the groups may be replaced by an oxygen atom.

Particularly preferable compounds as the component (E) are shown below. ##STR9##

In these compounds, R represents an alkyl group or an alkenyl group of 1 to 10 carbon atoms, and one carbon atom or two non-adjacent carbon atoms of the groups may be replaced by an oxygen atom.

The composition according to the present invention is preferred to contain at least one of the compounds expressed by the formula (I) in a proportion of 0.1 to 40% by weight in the aspect of superiority of the resulting liquid crystal characteristics.

The compound of the present invention can be obtained according to Wittig reaction (Organic Reaction Vol. 14, 270 (1965 ), that is, by reacting an aldehyde derivative expressed by the formula (II) ##STR10## wherein X represents a fluorineatom, trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, --A-- represents 1,4-cyclohexylene or 1,4-phenylene, --B-- represents 1,4-cyclohexylene, 1 represents 0, 1 or 2, m represents 0, 1 or 2, and l+m.gtoreq.1, Z represents --CH.sub.2 CH.sub.2 -- or a single bond and n represents an integer of 0 to 4, with a phosphorus ylide compound expressed by the formula (III)

wherein R represents a hydrogen atom or a linear or branched alkyl group of 1 to 7 carbon atoms and R' represents an alkyl group, an aryl group or an aralkyl group.

The compound of the present invention formed by the reaction of the compound of the formula (II) with that of the formula (III) is generally obtained in the form of a mixture of stereoisomers thereof, but the mixture can be separated for example according to a column chromatography. Further, if necessary, the mixture can be converted into the compound of the present invention according to a known method. Namely, by brominating the mixture with triphenylphosphinebromine and reducing the resulting halogenated compound, it is possible to convert to the mixture containing the compound of the present invention in a superior proportion.

In the process for producing the compound of the present invention, the reaction of the compound expressed by the formula (II) with that expressed by the formula (III) can be carried out according to a known method. For example, it is possible to use a compound (III) obtained by reacting the corresponding phosphonium compound with, as a preferable base, potassium t-butoxide, sodium methoxide, lithium diisopropylamide n-butyl lithium sodium hydride, pyridine, triethylamine or the like. This reaction and the succeeding reaction with the compound (II) is generally carried out in an organic solvent. As the solvent usable in the present reaction, those which do not hinder the reaction may be sufficient. For example, diethyl ether, tetrahydrofuran, dioxane, benzene, toluene, hexane, methylene chloride, chloroform, dimethylsulfoxide, dimethylformamide, etc. are preferable, and they can be used as a single solvent or a mixed solvent. The reaction temperature can be chosen from among the range of -50.degree. C. to the boiling point of the solvent used. The reaction is preferably carried out at -30.degree. C. to room temperature, but when the raw material concentration in the reaction mixture is high, the reaction should be carried out at -30.degree. C. to 0.degree. C.

The compound expressed by the formula (II) as a starting substance for preparing the compound of the present invention can be prepared according to various methods represented by the following (1) to (5): ##STR11##

In these formulas, R is as defined above, X represents a fluorine atom, trifluoromethyl group, trifluoromethoxy group or difluoromethoxy group, 1 represents 0, 1 or 2, m represents 0, 1 or 2, and l+m.gtoreq.1, --Z-- represents --CH.sub.2 CH.sub.2 -- or a single bond, n represents an integer of 1 to 4, n' represents n-1, and m' represents 0 or 1.

The compound of the present invention will be described in more detail by way of Examples, but it should not be construed to be limited thereto.

Preparation of 5-(4'-trans-(3",4",5"-trifluorophenyl)-cyclohexyl)-2E-pentene (Compound No. 1)

(1) Mg (17.1 g) was suspended in THF (100 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 3,4,5-trifluorobromobenzene (162 g) dissolved in THF (400 ml) to the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (100 g) dissolved in tetrahydrofuran (THF) (400 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH.sub.4 Cl (1 l) after completion of the reaction, extracting with ethyl acetate (1l), drying the organic layer over anhydrous MgSO.sub.4 and distilling off the solvent under reduced pressure, to obtain 1, 1-ethylenedioxy-4-hydroxy-4-(3',4',5'-trifluorophenyl)cyclohexane (166 2 g).

(2) 1,1-Ethylenedioxy-4-hydroxy-4-(3',4',5'-trifluoro-phenyl)cyclohexane (166.2 g) was dissolved in toluene (500 ml), followed by adding p-toluenesulfonic acidmonohydrate (20 g) into the solution, stirring the mixture under reflux for one hour, washing the reaction solution with water (500 ml), drying the organic layer over anhydrous magnesium sulfate, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(3',4',5'-trifluorophenyl)-3-cyclohexene (102.6 g).

(3) 1,1-Ethylenedioxy-4-(3,4',5'-trifluorophenyl)-3-cyclohexen (100 g) was dissolved in ethanol (1 l), followed by adding Pd/C (5%) (40 g), stirring the mixture in a hydrogen gas atmosphere to carry out a catalytic reduction, filtering off the catalyst after the reaction, and distilling off the organic layer under reduced pressure, to obtain 1,1-ethylenedioxy4-(3',4',5'-trifluorophenyl)-cyclohexane (95 g).

(4) Formic acid (82.7 g) and toluene (20 ml) were added to 1,1-ethylenedioxy-4-(3',4', 5'-trifluorophenyl)cyclohexane (95.02 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (500 ml), extracting with ethyl acetate (1 l), drying the organic layer over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and recrystallizing from ethanol, to obtain 4-(3',4',5'-trifluorophenyl)cyclohexanone (63.1 g). m.p. 123.5.degree. C.

(5) A suspension of 2-(1',3'-dioxan-2'-yl)ethyltriphenylphosphonium bromide (48.6 g) in THF (250 ml) was cooled down to 0.degree. C. with stirring in a nitrogen gas stream, followed by adding potassium-t-butoxide (14.9 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4 -(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (500 ml) after completion of the reaction, extracting with ethyl acetate (1 l), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure and subjecting to chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 3',4',5'-trifluorophenyl-4-(2'-(1,3-dioxan-2-yl)ethylidene)cyclohexane (24.9 g).

(6) 3',4',5'-trifluorophenyl-4-(2'-(1",3"-dioxan-2"-yl)ethylidene)cyclohexan ( 24.9 g) was dissolved in ethanol (200 ml), followed by adding Pd/C (5%) (15 g), stirring the mixture in a hydrogen gas atmosphere to carry out a catalytic reduction, filtering off the catalyst after completion of the reaction, distilling off the filtrate under reduced pressure and recrystallizing from ethanol according to a recrystallization procedure, to obtain 3+,4',5'-trifluorophenyl-4-(2'-(1",3"-dioxan-2"-yl)ethyl)-cyclohexane (13.2 g).

(7) Formic acid (10 g) and toluene (2 ml) were added to 3+,4',5'-trifluorophenyl-4-(2'-(1",3"-dioxan-2"-yl)ethyl)cyclohexan (13 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous magnesium sulfate and concentrating under reduced pressure, to obtain 3-(4'-(3",4",5"-trifluorophenyl)cyclohexyl)propionaldehyde (10.7 g).

(8) A suspension of ethyltriphenylphosphonium bromide (11.2 g) in THF (50 ml) was stirred in a nitrogen gas atmosphere, followed by cooling it down to 0.degree. C., adding potassium-t-butoxide (4.2 g) little by little, agitating the reaction solution at room temperature for one hour, dropwise adding a solution of 3-(4'-(3",4",5"-trifluorophenyl)cyclohexyl)propionaldehyde (67.8 g) in THF (20 ml), raising the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous magnesium sulfate, concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl-2-pentene (4.09 g).

(9) m-Chloroperbenzoic acid (7.7 g) and potassium carbonate (6.2 g) were fed into a solution of 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl-2-pentene (4.09 g) in methylene chloride (50 ml) to obtain a mixture, followed by stirring the mixture for 2 hours in an ice bath, adding water (50 ml), after completion of the reaction, extracting with methylene chloride (100 ml), drying the organic layer over anhydrous MgSO.sub.4 and concentrating it under reduced pressure to obtain 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl) -2,3-epoxypentane (3.84 g).

(10) Dibromotriphenylphosphine (12.3 g) was fed into a suspension of 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl)-2,3-epoxypentane (3.84 g) in benzene (100 ml) to obtain a mixture, followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl-2,3-dibromopentane (3.33 g).

(11) Zinc powder (3.2 g) was fed into a solution of 5-(4'-(3",4",5"-trifluorophenyl)cyclohexyl) -2,3-dibromopentane (3.33 g) in acetic acid (50 ml) to obtain a mixture, followed by stirring the mixture at room temperature over night, filtering off solids after completion of the reaction, adding the filtrate to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 5-(4'-(3",4",5"-trifluorophenyl) cyclohexyl)-2E-pentene (320 mg). m.p. 13.8.degree.-16.9.degree. C.

Preparation of 4-trans-(3',4',5'-trifluorophenyl)cyclohexylethene (Compound No. 2)

(1) A suspension of methoxymethyltriphenylphosphonium chloride (36.4 g) in THF (200 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (12 g) little by little, while cooling the suspension at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluorophenyl)methoxymethylenecyclohexane (18.25 g).

(2) THF (40 ml) and 2N hydrochloric acid (20 ml) were added to 4-(3',4',5'-trifluorophenyl)methoxymethylenecyclohexane (14.5 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO.sub.4, and concentrating under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)cyclohexanecarbaldehyde (6.5 g).

(3) A suspension of methyltriphenylphosphonium bromide (2.7) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.1 g) little by little, while cooling the suspension at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanecarbaldehyde (1.5 g) in THF (5 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 4-trans-(3',4',5'-trifluorophenyl)cyclohexylethene (1.05 g). m.p. 20.3.degree.-21.3.degree. C.

Preparation of 4-trans-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexylethene (Compound No. 3)

(1) Mg (3.4 g) was suspended in THF (20 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 3,5-difluoro-4-trifluoromethylbromobenzene (40 g) in THF (100 ml) to the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (20 g) in THF (100 ml), stirring the mixture at room temperature for one adding a saturated aqueous solution of NH.sub.4 Cl (200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO.sub.4, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-hydroxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyc lohexane (23 g).

(2) 1,1-Ethylenedioxy-4-hydroxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyc lohexane (23 g) was dissolved in toluene (200 ml), followed by adding p-toluenesulfonic acidmonohydrate (5 g) to the solution, stirring the mixture under reflux for one hour, allowing the mixture to cool down, washing the reaction solution with water (200 ml), drying the organic layer over anhydrous MgSO.sub.4, and distilling off the solvent, to obtain 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)-3-cyclohexen e (17.3 g).

(3) 1,1-Ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)-3-cyclohexen e (17.3 g) was dissolved in ethanol (200 ml), followed by adding Pd/C (5%) (5 g), carrying out a catalytic reduction with stirring in a hydrogen gas atmosphere, filtering off the catalyst after completion of the reaction, and distilling off the organic layer under reduced pressure, to obtain 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (15.7 g).

(4) Formic acid (11.3 g) and toluene (5 ml) were added to 1,1-ethylenedioxy-4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexane (15.7 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, and distilling off the solvent under reduced pressure, to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanone (12.0 g).

(5) A suspension of methoxymethyltriphenylphosphonium chloride (7 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (2.9 g) little by little, while cooling the suspension at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanone (4.7 g) in THF (30 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating it under reduced pressure, and carrying out chromatography treatment on silica gel, with ethyl acetate/heptane (1:5), to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)methoxymethylenecyclohexane (2.06 g).

(6) THF (10 ml) and 2N hydrochloric acid (10 ml) were added to 4-(3',5'-difluoro-4'-trifluoromethylphenyl)methoxymethylenecyclohexane (2.06 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (20 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO.sub.4, and concentrating under reduced pressure, to obtain 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanecarbaldehyde (1.99 g).

(7) A suspension of methyltriphenylphosphonium bromide (3 ) in THF (10 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.2 g) little by little, while cooling the suspension at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding solution of 4-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexanecarbaldehyde (1.99 g) in THF (5 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (20 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 4-trans-(3',5'-difluoro-4'-trifluoromethylphenyl)cyclohexylethene (300 mg).

The following compounds are prepared according to the above-mentioned procedure:

4. 3-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-2E-propene

5. 3-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-1-propene

6. 4-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-1-butene m.p. 16.8.degree.-19.3.degree. C.

7. 4-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-2E-butene

8. 4-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-3E-butene

9. 5-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-1-pentene

10. 5-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-3E-pentene

11. 5-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-4E-pentene

12. 6-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-1-hexene

13. 5-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-2E-hexene

14. 6-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-3E-hexene

15. 5-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-4E-hexene

16. 7-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-2E-heptene

17. 7-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-3E-heptene

18. 7-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-4E-heptene

19. 8-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-3E-octene

20. 8-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-4E-octene

21. 9-(4'-trans-(3",4",5"-trifluorophenyl)cyclohexyl)-4E-nonene

22. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-2E-propen e

23. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-1-propene

24. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-1-butene

25. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-2E-butene

26. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-3E-butene

27. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-1-pentene

28. 5-(4'-trans-(3",5"-difluoro-4"-trifluorcmEthylphenyl)cyclohexyl)-2E-penten e

29. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-3-pentene

30. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-4E-penten e

31. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-1-hexene

32. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-2E-hexene

33. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-3E-hexene

34. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-4E-hexene

35. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-2E-hepten e

36. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-3E-hepten e

37. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-4E-hepten e

38. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-3E-octene

39. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-4E-octene

40. 9-(4'-trans-(3",5"-difluoro-4"-trifluoromethylphenyl)cyclohexyl)-4E-nonene

41. 2-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl) ethene

42. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-2E-prop ene

43. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-1-prope ne

44. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-1-buten e

45. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-2E-bute ne

46. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-3E-bute ne

47. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-1-pente ne

48. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-2E-pent ene

49. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-3E-pent ene

50. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-4E-pent ene

51. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-1-hexen e

52. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-2E-hexe ne

53. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-3E-hexe ne

54. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-4E-hexe ne

55. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-2E-hept ene

56. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-3E-hept ene

57. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-4E-hept ene

58. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-3E-octe ne

59. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-4E-octe ne

60. 9-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxylphenyl)cyclohexyl)-4E-none ne

61. 2-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)ethene

62. 3-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-2E-prope ne

63. 3-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-1-propen e

64. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-1-butene

65. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-2E-buten e

66. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-3E-buten e

67. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-1-penten e

68. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-2E-pente ne

69. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-3E-pente ne

70. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-4E-pente ne

71. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-1-hexene

72. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-2E-hexen e

73. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-3E-hexen e

74. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-4E-hexen e

75. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-2E-hepte ne

76. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-3E-hepte ne

77. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-4E-hepte ne

78. 8-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-3E-octen e

79. 8-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-4E-octen e

80. 9-(4'-trans-(3",5"-difluoro-4"-difluoromethoxylphenyl)cyclohexyl)-4E-nonen e.

Preparation of 2-(4'-trans-(4"-trans-(3'",4'", 5'"-trifluorophenyl)cyclohexyl)cyclohexyl)ethene (Compound No. 81 )

(1) Flaked Mg (11.6 g, 0.477 mol) was placed in a 21 capacity, three-neck flask, followed by adding THF (100 ml) in a nitrogen gas stream, dropwise adding a solution of 3,4,5-trifluorobromobenzene (91.6 g, 0.434 mol) in THF (200 ml) with stirring at a velocity of keeping 30.degree. C., stirring the mixture at room temperature for 2 hours after completion of the dropwise addition, dropwise adding to the reaction solution, a solution of 4,4'-dicyclohexanedionemonoethylene acetal (94 g, 0.395 mol) in THF (200 ml) over 45 minutes so as to keep its temperature at 30.degree. C. or lower, stirring the mixture at room temperature for 2 hours after completion of the dropwise addition, allowing the reaction solution to stand overnight, again stirring the reaction solution, adding a saturated aqueous solution of NH.sub.4 Cl little by little, extracting the resulting solution three times with ethyl acetate (400 ml), washing the organic layer with water, drying it over anhydrous MgSO.sub. 4, and concentrating under reduced pressure, to obtain 4-hydroxy-4-(3',4',5'-trifluorophenyl)dicyclohexaneethylene acetal (125 g, GC 79%) in the form of yellow-brown solids. This product was used for the subsequent reaction without purification.

(2) The above reaction product (125 g) was dissolved in toluene (500 ml), in a 2 1 capacity three-neck flask equipped with Dean-Stark's device, followed by adding Amberlist-15 (6.5 g), heating the mixture under reflux with stirring for 4 hours, cooling the solution down to room temperature after completion of the reaction, filtering off the Amberlist-15, concentrating the mother liquor under reduced pressure and separating and purifying the residue according to silica gel chromatography, to obtain 4-(3', 4',5'-trifluorophenyl)-3'-dicyclohexen-4-one ethylene acetal (85 g). m.p. 107.0.degree.-114.0.degree. C.

(3) 4-(3',4',5'-Trifluorophenyl)-3'-dicyclohexen-4-one ethylene acetal (66 g) was placed in a 1 l capacity three-neck flask and dissolved in a mixed solvent of ethyl acetate/ethanol (3:1) (500 ml), followed by adding Pd/C (5 wt %) catalyst (5 g) to the solution, stirring the mixture in a hydrogen gas atmosphere, completing the stirring when absorption of the hydrogen gas was not observed, filtering off the catalyst and concentrating the resulting solution under reduced pressure, to obtain a transparent oily substance. This substance was recrystallized from ethanol and purified, to obtain trans-4-(3',4',5'-trifluorophenyl)dicyclohexane-4-one ethylene acetal (24 g). m.p. 101.0.degree.-104.5.degree. C.

(4) Trans-4-(3',4',5'-trifluorophenyl)-dicyclohexan-4one ethylene acetal (24 g) was placed in a 200 ml capacity, egg-plant type flask, followed by dissolving it in toluene (100 ml), adding formic acid (15.6 g) to the solution, heating the mixture under reflux with stirring for 4 hours, cooling it down to room temperature after completion of the reaction, adding ethyl acetate (200 ml), washing with water, drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure to obtain white crystals, and recrystallizing them from n-heptane for purification, to obtain 4-(trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)cyclohexanone (17 g). m.p. 96.7.degree.-99.6.degree. C.

(5) Methoxymethyltriphenylphosphonium chloride (16.5 g) was placed in a 300 ml capacity three-neck flask, and added THF (100 ml) to obtain a suspension, followed by adding potassium-t-butoxide (6.5 g) to the suspension while keeping the temperature at -10.degree. C. or lower, stirring the mixture at -10.degree. C. for one hour, dropwise adding a solution of 4-(trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)cyclohexanone (10 g) in THF (80 ml) at a speed of keeping -10.degree. C., stirring the mixture at the temperature for one hour, further stirring at room temperature for 2 hours, adding water (100 ml) after completion of the reaction, extracting three times with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4, concentrating under reduced pressure to obtain white solids, and isolating and purifying them according to silica gel column chromatography, to obtain 4-(trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)methoxymethylenecyclohexa ne (10.2 g ) (white crystals). m.p. 78.4.degree. -81.2.degree. C.

(6) 4-(Trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)methoxymethylenecyclohexa ne (10.2 g) was placed in a 300 ml capacity egg-plant type flask, followed by adding THF (80 ml) to obtain a solution, adding 2N-hydrochloric acid (30 ml) to the solution, heating the mixture with stirring for 2 hours, cooling down to room temperature after completion of the reaction, adding water (30 ml), extracting three times with ethyl acetate (50 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4, and concentrating under reduced pressure, to obtain 4-(trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)cyclohexanecarbaldehyde (6 g) (a transparent oily substance). This product was used for the subsequent reaction without purification.

(7) Methyltriphenylphosphonium bromide (14.0 g) was placed in a 300 ml capacity three-neck flask, followed by adding THF (100 ml) to obtain a suspension, adding potassium-t-butoxide (5.3 g) to the suspension while keeping a temperature of -10.degree. C. or lower, stirring the mixture at -10.degree. C. for one hour, dropwise adding a solution of 4-(trans-4'-(3",4",5"-trifluorophenyl)cyclohexyl)cyclohexanecarbaldehyde (8.5 g) in THF (100 ml) at a speed of keeping -10.degree. C., stirring the mixture at the temperature for one hour, further stirring at room temperature for 2 hours, adding water (100 ml) after completion of the reaction, extracting three times with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4 and concentrating under reduced pressure to obtain white solids. The aimed product was isolated from the solids according to silica gel column chromatography, recrystallized and purified to obtain trans-(4-(trans-4' -(3",4",5"-trifluorophenyl)cyclohexyl)cyclohexylethene (3.8 g) (white crystals). This product exhibited liquid crystal phases: C-N point, 57.1.degree.-58.8.degree. C. and N-I point, 69.2.degree.-71.3.degree. C.

The following compounds are prepared according to the above procedure:

82. 3-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 2E-propene

83. 3-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 1-propene

84. 4-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 1-butene C-N point, 64.1.degree. C. and N-I point, 99.1.degree. C.

85. 4-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 2E-butene

86. 4-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 3E-butene

87. 5-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 1-pentene

88. 5-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 2E-pentene

89. 5-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 3E-pentene

90. 5-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 4E-pentene

91. 6-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 1-hexene

92. 6-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 2E-hexene

93. 6-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 3E-hexene

94. 6-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 4E-hexene

95. 7-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 2E-heptene

96. 7-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 3E-heptene

97. 7-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 4E-heptene

98. 8-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 3E-octene

99. 8-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 4E-octene

100. 9-(4'-trans-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)cyclohexyl)- 4E-nonene

101. 2-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)ethene

102. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-2E-propene

103. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-1-propene

104. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-1-butene

105. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-2E-butene

106. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-3E-butene

107. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-1-pentene

108. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-2E-pentene

109. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-3E-pentene

110. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-4E-pentene

111. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-1-hexene

112. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-2E-hexene

113. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-3E-hexene

114. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-4E-hexene

115. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-2E-heptene

116. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-3E-heptene

117. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-4E-heptene

118. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-3E-octene

119. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)-4E-octene

120. 9-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)cyclohex yl)cyclohexyl)- 4E-nonene

121. 2-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)ethene

122. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-2E-propene

123. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-1-propene

124. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-1-butene

125. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-2E-butene

126. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-3E-butene

127. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-1-pentene

128. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-2E-pentene

129. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-3E-pentene

130. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl-4E-pentene

131. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-1-hexene

132. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-2E-hexene

133. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-3E-hexene

134. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-4E-hexene

135. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-2 E-heptene

136. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-3E-heptene

137. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-4E-heptene

138. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-3E-octene

139. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-4E-octene

140. 9-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-trifluoromethoxyphenyl)cyclohe xyl)cyclohexyl)-4E-nonene

141. 2-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)ethene

142. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-2E-propene

143. 3-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-1-propene

144. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-1-butene

145. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-2E -butene

146. 4-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-3E-butene

147. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-1-pentene

148. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-2E-pentene

149. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-3E-pentene

150. 5-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-4E-pentene

151. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-1-hexene

152. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-2E-hexene

153. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-3E-hexene

154. 6-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-4E-hexene

155. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-2E-heptene

156. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-3E-heptene

157. 7-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-4E-heptene

158. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-3E-octene

159. 8-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-4E-octene

160. 9-(4'-trans-(4"-trans-(3'",5'"-difluoro-4'"-difluoromethoxyphenyl)cyclohex yl)cyclohexyl)-4E-nonene

Preparation of 2-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)ethene (Compound No. 161)

(1) A suspension of 3,4,5-trifluorobenzyltriphenylphosphonium bromide (234 g) in THF (500 ml) was stirred in a nitrogen gas stream, followed by adding sodium methoxide (32.4 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-formylcyclohexanone (50 g) in THF (250 ml), stirring the mixture at room temperature for 2 hours, adding it to water (1 l) extracting with ethyl acetate (1 1), washing the organic layer with water, drying over anhydrous MgSO.sub.4, concentrating the solvent under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethenyl)cyclohexanone (71 g).

(2) 4-(2'-(3",4",5"-Trifluorophenyl)ethenyl)cyclohexanone (71 g) was dissolved in ethanol (500 ml), followed by adding Pd/C (5%) (2.0 g), hydrogenating the compound in a hydrogen gas atmosphere with stirring till the hydrogen absorption was completed, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethyl)cyclohexanone (70 g).

(3) A suspension of methoxymethyltriphenylphosphonium chloride (112.3 g) in THF (300 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (45.4 g) little by little while cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding 4-(2'-(3",4",5"-trifluorophenyl)ethyl)cyclohexanone (70 g)in THF (200 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (500 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethyl)methoxymethylenecyclohexane (53.7 g).

(4) THF (100 ml) and 2N-hydrochloric acid (100 ml) were added to 4-(2'-(3",4",5"-trifluorophenyl)ethyl)methoxymethylenecyclohexane (20 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (300 ml) after completion of the reaction, extracting with ethyl acetate (300 ml), drying the organic layer over anhydrous MgSO.sub.4 and concentrating under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluorophenyl)ethyl)cyclohexane carbaldehyde (17 g).

(5) A suspension of methyltriphenylphosphonium bromide (27 W) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide little by little under cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(3",4",5"-trifluorophenyl)ethyl)cyclohexanecarbaldehyde (17 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring it for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and crystallizing from heptane, to obtain 2-(4'-trans-(2"-(3'",4 '",5'"-trifluorophenyl)ethyl)cyclohexyl)ethene (9 g).

The following compounds are prepared according to the above procedure:

162. 3-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-1-propene

163. 3-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-2E-propene

164. 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-1-butene

165. 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-2E-butene

166. 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-3E-butene

167. 5-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-1-pentene

168. 5-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-2E-pentene

169. 5-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-3E-pentene

170. 5-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-4E-pentene

171. 6-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)1-hexene

172. 6-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-2E-hexene

173. 6-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-3E-hexene

174. 6-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-4E-hexene

175. 7-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-2E-heptene

176. 7-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-3E-heptene

177. 7-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-4E-heptene

178. 8-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-3E-octene

179. 8-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-4E-octene

180. 9-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)-4E-nonene

181. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)ethene

182. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-2E-propene

183. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-1-propene

184. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-1-butene

185. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-2E-butene

186. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-3E-butene

187. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-1-pentene

188. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-2E-pentene

189. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-3E-pentene

190. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-4E-pentene

191. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl) -1-hexene

192. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-2E-hexene

193. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-3E-hexene

194. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-4E-hexene

195. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-2E-heptene

196. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-3E-heptene

197. 7-(4'-trans-(2'-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-4E-heptene

198. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-3E-octene

199. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-4E-octene

200. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethylphenyl)ethyl)cyclohex yl)-4E-nonene

201. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)ethene

202. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-2E-propene

203. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)-ethyl)cyclo hexyl)-1-propene

204. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-1-butene

205. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-2E-butene

206. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-3E-butene

207. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-1-pentene

208. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-2E-pentene

209. 5-(4'-trans-(2"-(3'", 5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cyclohexyl)-3E-pentene

210. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-4E-pentene

211. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-1-hexene

212. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-2E-hexene

213. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-3E-hexene

214. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl -4 E-hexene

215. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-2E-heptene

216. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-3E-heptene

217. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-4E-heptene

218. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-3E-octene

219. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-4E-octene

220. 9-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxylphenyl)ethyl)cycloh exyl)-4E-nonene

221. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)ethene

222. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-2E-propene

223. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-1-propene

224. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-1-butene

225. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-2E-butene

226. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-3E-butene

227. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-1-pentene

228. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-2E-pentene

229. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-3E-pentene

230. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-4E-pentene

231. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-1-hexene

232. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-2E-hexene

233. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-3E-hexene

234. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-4E-hexene

235. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-2E-heptene

236. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-3E-heptene

237. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-4E-heptene

238. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-3E-octene

239. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-4E-octene

240. 9-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxylphenyl)ethyl)cyclohe xyl)-4E-nonene

Preparation of 2-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)ethene (Compound No. 241)

(1) A suspension of triethyl phosphonoacetate (21.8 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (11.8 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)cyclohexanone (20 g) in THF (50 ml), stirring at room temperature for 2 hours, adding to water (100 ml), extracting with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4 and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl))ethoxycarbonylmethylenecyclohexane (18.3 g).

(2) 4-(3',4',5'-Trifluorophenyl)ethoxycarbonylmethylenecyclohexane (18.3 g) was dissolved in ethanol (100 ml), followed by adding Pd/C (5%, 5 g), stirring the mixture, hydrogenating in a hydrogen gas atmosphere until completion of absorption of a hydrogen, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4 -(3',4',5'-trifluorophenyl)ethoxycarbonylmethylcyclohexane (17.2 g).

(3) Lithiumaluminium hydride (2.2 g) was added to a solution of 4-(3',4',5'-trifluorophenyl)ethoxycarbonylmethylcyclohexane (17.2 g) in THF (100 ml), followed by stirring the mixture at room temperature for 2 hours, adding ethyl acetate (100 ml) little by little after completion of the reaction, further adding 2N hydrochloric acid (50 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4 and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)-1-(2'hydroxyethyl)cyclohexane (10.4 g).

(4) 4-(3',4',5'-Trifluorophenyl)-1-(2'-hydroxyethyl)cyclohexane (10.4 g) was added to an aqueous solution of 47% HBr (15 ml), followed by stirring the mixture under reflux for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (100 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4, and concentrating the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluorophenyl)-1 -(2'-bromoethyl)cyclohexane (10.4g).

(5) Mg (0.7 g) was suspended in THF (10 ml) in a nitrogen gas stream, followed by dropwise adding a solution of 4-(3',4',5'-trifluorophenyl)-1 -(2'-bromoethyl)cyclohexane (9.8 g) in THF (50 ml), into the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,4-cyclohexanedionemonoethylene ketal (4 g) in THF (30 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH.sub.4 Cl (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4 and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-hydroxy-4-(2'-(4"-(3'",4'", 5'"-trifluorophenyl)cyclohexyl)ethyl-cyclohexane 8.2 g).

(6) p-Toluenesulfonic acidmonohydrate (1 g) was added to a solution of 1,1-ethylenedioxy-4-hydroxy-4-(2'-(4"-(3'",4'", 5'"-trifluorophenyl)cyclohexyl)ethylcyclohexane (8.2 g) in toluene (100 ml), followed by stirring the mixture under reflux for one hour, washing the reaction solution with water (100 ml), drying the organic layer over anhydrous MgSO.sub.4, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-(2'-(4"-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)-3 -cyclohexene (6.7 g).

(7) Pd/C (5% ) (1 g) was added to a solution of 1,1-ethylenedioxy -(2'-(4"-(3'",4'",5'"-trifluorophenyl)cyclohexyl)-ethyl)-3-cyclohexene (6.7 g) in ethanol (200 ml), followed by carrying out catalytic reduction in a hydrogen gas atmosphere, filtering off the catalyst after completion of the reaction and distilling off the solvent from the organic layer under reduced pressure, to obtain 1,1 -ethylenedioxy-(2'-(4"-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cyclo hexane (6.2 g).

(8) Formic acid (5 g, and toluene (2 ml) were added to 1,1-ethylenedioxy-(2'-(4"-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cy clohexane (6.2 g), followed by heating the mixture under reflux with stirring for 2 hours, pouring the reaction solution into water (20 ml), extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO.sub.4, distilling off the solvent under reduced pressure, and recrystallizing from ethanol, to obtain 4-(2'-(4"-trans (3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cyclohexanone (4.9 g).

(9) A suspension of methoxymethyltriphenylphosphonium chloride (6.2 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (2 g) little by little while cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cyclohexanon e (4.9 g) in THF (20 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, and carrying out chromatography treatment in silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)methoxymethy lenecyclohexane 3.8 g).

(10) THF (10 ml) and 2N hydrochloric acid (10 ml) were added to 4-(2'-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)methoxymethy lenecyclohexane (3.8 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO.sub.4 and concentrating under reduced pressure, to obtain 4-(2'-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cyclohexanec arbaldehyde (3.5 g).

(11) A suspension of methyltriphenylphosphonium bromide (3.5 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by cooling it down to 0.degree. C., adding potassium-t-butoxide (13 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(4"-trans-(3'",4'",5'"-trifluorophenyl)cyclohexyl)ethyl)cyclohexanec arbaldehyde (3.5 g) in THF (20 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (50 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)ethene (2.2g).

The following compounds are prepared according to the above procedure:

242. 3-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-1-propene

243. 3-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-2E-propene

244. 4-(4'-trans-(2"-(4'"-trans-(3"", 4"",5""-trifluorophenyl)cyclohexyl)ethyl)cyclohexyl)-1-butene

245. 4-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-2E-butene

246. 4-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-3E-butene

247. 5-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-1-pentene

248. 5-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-2E-pentene

249. 5-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-3E-pentene

250. 5-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-4E-pentene

251. 6-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-1-hexene

252. 6-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-2E-hexene

253. 6-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-3E-hexene

254. 6-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-4E-hexene

255. 7-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-2E-heptene

256. 7-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-3E-heptene

257. 7-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-4E-heptene

258. 8-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-3E-octene

259. 8-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-4E-octene

260. 9-(4'-trans-(2"-(4'"-trans-(3"",4"",5""-trifluorophenyl)cyclohexyl)ethyl)c yclohexyl)-4E-nonene

261. 2-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)ethene

262. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-propene

263. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-propene

264. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-butene

265. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-butene

266. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-butene

267. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-pentene

268. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-pentene

269. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-pentene

270. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-pentene

271. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-hexene

272. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-hexene

273. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-hexene

274. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-hexene

275. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-heptene

276. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-heptene

277. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-heptene

278. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-octene

279. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-octene

280. 9-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethylphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-nonene

281. 2-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)ethene

282. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-2E-propene

283. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""trifluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-propene

284. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-1-butene

285. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-2E-butene

286. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-3E-butene

287. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)1-pentene

288. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-2E-pentene

289. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-3E-pentene

290. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-4E-pentene

291. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-1-hexene

292. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-2E-hexene

293. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-3E-hexene

294. 6-(4'-trans-(2"-(4""-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-4E-hexene

295. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-2E-heptene

296. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-3E-heptene

297. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-4E-heptene

298. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-3E-octene

299. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-4E-octene

300. 9-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)cy clohexyl)ethyl)cyclohexyl)-4E-nonene

301. 2-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)ethene

302. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-propene

303. 3-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)1-propene

304. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-butene

305. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-butene

306. 4-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-butene

307. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-1-pentene

308. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""difluoromethoxyphenyl)cycl ohexyl)ethyl)cyclohexyl)-2E-pentene

309. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""difluoromethoxyphenyl)cycl ohexyl)ethyl)cyclohexyl)-3E-pentene

310. 5-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-pentene

311. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""difluoromethoxyphenyl)cycl ohexyl)ethyl)cyclohexyl)-1-hexene

312. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-hexene

313. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-hexene

314. 6-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""difluoromethoxyphenyl)cycl ohexyl)ethyl)cyclohexyl)-4E-hexene

315. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-2E-heptene

316. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-3E-heptene

317. 7-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E- heptene

318. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-3m-octene

319. 8-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-4 E-octene

320. 9-(4'-trans-(2"-(4'"-trans-(3"",5""-difluoro-4""-difluoromethoxyphenyl)cyc lohexyl)ethyl)cyclohexyl)-4E-nonene

Preparation of 2-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)ethene (Compound No. 321)

(1) A suspension of 3,4,5-trifluorobenzyltriphenylphosphonium bromide (51.5 g) in THF (100 ml) was stirred in a nitrogen gas stream, followed by adding sodium methoxide (6.2 g) little by little at room temperature, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-formylcyclohexyl)cyclohexanone (20 g) in THF(50 ml), stirring the mixture at room temperature for 2 hours, adding to water (500 ml), extracting with ethyl acetate (500 ml), washing the organic layer with water, drying over anhydrous MgSO.sub.4, and concentrating the solvent under reduced pressure, to obtain, 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethenyl)cyclohexyl)cyclohexan one (22.5 g).

(2) 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethenyl)cyclohexyl)cyclohexan one (22.5 g) was dissolved in ethanol (250 ml), followed by adding Pd/C (5% ) (5 g), stirring the mixture, hydrogenating in a hydrogen gas atmosphere till completion of absorption of a hydrogen gas, filtering off the catalyst after completion of the reaction, and concentrating the solvent under reduced pressure, to obtain 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)cyclohexanon e (20.4 g).

(3) A suspension of methoxymethyltriphenylphosphonium chloride (23 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by cooling it down to 0.degree. C., adding potassium-t-butoxide (8.2 g) little by little, stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)cyclohexanon e(20.4 g) in THF (100 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, pouring into water (250 ml) after completion of the reaction, extracting with ethyl acetate (250 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)methoxymethy lenecyclohexane (15.6 g).

(4) THF (30 ml) and 2N hydrochloric acid (30 ml) were added to 4-(4'-trans-(2'-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)methoxymethy lenecyclohexane (15.6 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, and concentrating under reduced pressure, to obtain 4 (4'-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)cyclohexanecarbaldeh yde (13.7 g).

(5) A suspension of methyltriphenylphosphonium bromide (15.2 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (5.3 g) little by little while cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(4'-trans-(2"-(3'",4'",5'"-trifluorophenyl)ethyl)cyclohexyl)cyclohexanec arbaldehyde (13.7 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)e thene (8.2 g).

The following compounds are prepared according to the above procedure:

322. 3-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-1-propene

323. 3-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-2E-propene

324. 4-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-1-butene

325. 4-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-2E-butene

326. 4-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-3E-butene

327. 5-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-1-pentene

328. 5-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-2E-pentene

329. 5-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-3E-pentene

330. 5-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-4E-pentene

331. 6-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-1-hexene

332. 6-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-2E-hexene

333. 6-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-3E-hexene

334. 6-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-4E-hexene

335. 7-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-2E -heptene

336. 7-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-3E-heptene

337. 7-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-4E-heptene

338. 8-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-3E-octene

339. 8-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-4E-octene

340. 9-(4'-trans-(4"-trans-(2'"-(3"",4"",5""-trifluorophenyl)ethyl)cyclohexyl)c yclohexyl)-4E-nonene

341. 2-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)ethene

342. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-propene

343. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-1-propene

344. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-1-butene

345. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-butene

346. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-butene

347. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-1-pentene

348. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""trifluoromethyl-phenyl)eth yl)cyclohexyl)cyclohexyl)-2E-pentene

349. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""phenyl)ethyl)cyclohexyl)cy clohexyl)-3E-pentene

350. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-pentene

351. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-1-hexene

352. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""trifluoromethylphenyl)ethy l)cyclohexyl)cyclohexyl)-2E-hexene

353. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-hexene

354. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-hexene

355. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethyl)ethyl)cyc lohexyl)cyclohexyl)-2E-heptene

356. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-heptene

357. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-heptene

358. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""trifluoromethylphenyl)ethy l)cyclohexyl)cyclohexyl)-3E-octene

359. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-octene

360. 9-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethylphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-nonene

361. 2-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxy)ethyl)cy clohexyl)cyclohexyl)ethene

362. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-2E-propene

363. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-1-propene

364. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-1-butene

365. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-2E-butene

366. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-3E-butene

367. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-1-pentene

368. 5-(4'-trans-(4"-trams-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-2E-pentene

369. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-3E-pentene

370. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-4E-pentene

371. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-1-hexene

372. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-2E-hexene

373. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-3E-hexene

374. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-4E-hexene

375. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-2E-heptene

376. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-3E-heptene

377. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-4E-heptene

378. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-3E-octene

379. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-4E-octene

380. 9-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-trifluoromethoxyphenyl)et hyl)cyclohexyl)cyclohexyl)-4E-nonene

381. 2-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)ethene

382. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-propene

383. 3-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""difluoromethoxyphenyl)ethy l)cyclohexyl)cyclohexyl)-1-propene

384. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-1-butene

385. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-butene

386. 4-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-butene

387. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-1-pentene

388. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-pentene

389. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-pentene

390. 5-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-pentene

391. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-1-hexene

392. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-hexene

393. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-hexene

394. 6-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-hexene

395. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-2E-heptene

396. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-heptene

397. 7-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-heptene

398. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-3E-octene

399. 8-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-octene

400. 9-(4'-trans-(4"-trans-(2'"-(3"",5""-difluoro-4""-difluoromethoxyphenyl)eth yl)cyclohexyl)cyclohexyl)-4E-nonene

Preparation of 2-(4'-trans-(3",4",5"trifluoro-4'"-biphenyl)cyclohexyl)ethene (Compound No. 401)

(1) 4-(3",4",5"-Trifluorophenyl)-3'-dicyclohexen-4-one ethylene acetal (20 g) and DDQ (2,3-dichloro-5,6-dicyanobenzoquinone) (16.7 g) were dissolved in toluene (200 ml), followed by stirring the solution under reflux for 4 hours, filtering off deposited insolubles, washing the organic layer with water, drying over anhydrous MgSO.sub.4, distilling off the solvent under reduced pressure, and purifying the resulting raw product according to column chromatography using silica gel (eluting solvent: ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluoro-4'-biphenyl)cyclo-hexan-4-one ethylene acetal (13.9 g).

(2) Formic acid (10 g) and toluene (2 ml) were added to 4-(3',4',5'-trifluoro-4"-biphenyl)cyclohexan-4-one ethylene acetal (13.9 g), followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (50 ml), drying the organic layer over anhydrous MgSO.sub.4 and distilling off the solvent under reduced pressure, to obtain 4-(3',4',5'-trifluoro-4"-biphenyl)cyclohexanone (11.5 g).

(3) A suspension of methoxymethyltriphenylphosphonium chloride (13.6 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (48 g) little by little while cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluoro-4"-biphenyl)cyclohexanone (11.5 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(3',4',5'-trifluoro-4"-biphenyl)methoxymethylenecyclohexane (8.8 g).

(4) THF (50 ml) and 2N hydrochloric acid (50 ml) were added to 4-(3',4',5'-trifluoro-4"-biphenyl)methoxymethylene cyclohexane (8.8 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4 and concentrating under reduced pressure, to obtain 4-(3',4',5'-trifluoro-4"-biphenyl)cyclohexanecarbaldehyde (7.5 g).

(5) A suspension of methyltriphenylphosphonium bromide (9 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (3.1 g) little by little while cooling at 0.degree. C., stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(3',4',5'-trifluoro-4"-biphenyl)cyclohexanecarbaldehyde (7.5 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), and recrystallizing from heptane, to obtain 2-(4'-trans-(3",4",5"-trifluoro-4'"-biphenyl)cyclohexyl)ethene (4.6 g).

The following compounds are prepared according to the above procedure:

402. 3-(4'-trans-(3",4",5'-trifluoro-4'"biphenylyl)cyclohexyl)-1-propene

403. 3-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-2E-propene

404. 4-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-1-butene

405. 4-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-2E-butene

406. 4-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-3E-butene

407. 5-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-1-pentene

408. 5 (4'-trans-(3",4",5"-trifluoro-4'"biphenylyl)cyclohexyl)-2E-pentene

409. 5-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-3E-pentene

410. 5-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-4E-pentene

411. 6-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-1-hexene

412. 6-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-2E-hexene

413. 6-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-3E-hexene

414. 6-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-4E-hexene

415. 7-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-2E-heptene

416. 7-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-3E-heptene

417. 7-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-4E-heptene

418.8-(4 '-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-3E-octene

419. 8-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-4E-octene

420. 9-(4'-trans-(3",4",5"-trifluoro-4'"-biphenylyl)cyclohexyl)-4E-nonene

421. 2-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)e thene

422. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 2E-propene

423. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 1-propene

424. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 1-butene

425. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 2E-butene

426. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 3E-butene

427. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 1-pentene

428. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 2E-pentene

429. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 3E-pentene

430. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 4E-pentene

431. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 1-hexene

432. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 2E-hexene

433. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 3E-hexene

434. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 4E-hexene

435. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 2E-heptene

436. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 3E-heptene

437. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 4E-heptene

438. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 3E-octene

439. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 4E-octene

440. 9-(4'-trans-(3",5"-difluoro-4"-trifluoromethyl-4'"-biphenylyl)cyclohexyl)- 4E-nonene

441. 2-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) ethene

442. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -2E-propene

443. 3-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -1-propene

444. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -1-butene

445. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -2E-butene

446. 4-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -3E-butene

447. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -1-pentene

448. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -2E-pentene

449. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -3E-pentene

450. 5-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)-cyclohexyl )-4E-pentene

451. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl )cyclohexyl)-1-hexene

452. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -2E-hexene

453. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -3E-hexene

454. 6-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -4E-hexene

455. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -2E-heptene

456. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)-cyclohexyl )-3E-heptene

457. 7-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -4E-heptene

458. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -3E-octene

459. 8-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -4E-octene

460. 9-(4'-trans-(3",5"-difluoro-4"-trifluoromethoxy-4'"-biphenylyl)cyclohexyl) -4E-nonene

461. 2-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)e thene

462. 3-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 2E-propene

463. 3-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)-cyclohexyl) -1-propene

464. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl) -1-butene

465. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 2E-butene

466. 4-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 3E-butene

467. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 1-pentene

468. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 2E-pentene

469. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 3E-pentene

470. 5-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 4E-pentene

471. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 1-hexene

472. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 2E-hexene

473. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 3E-hexene

474. 6-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 4E-hexene

475. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 2E-heptene

476. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 3E-heptene

477. 7-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 4E-heptene

478. 8-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 3E-octene

479. 8-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 4E-octene

480. 9-(4'-trans-(3",5"-difluoro-4"-difluoromethoxy-4'"-biphenylyl)cyclohexyl)- 4E-nonene

Preparation of 2-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"biphenyl)ethyl)cyclohexyl)ethene (Compound No. 481).

(1) Mg (2 g) was suspended in THF (10 ml) in a nitrogen gas stream, followed by dropwise adding a solution of3,4,5-trifluorobromobenzene (19.0 g) in THF (150 ml), into the suspension, stirring the mixture at room temperature for one hour, dropwise adding a solution of 1,1-ethylenedioxy-4-(2'-(4"-oxocyclohexyl)ethyl)cyclohexane (20 g) in THF (50 ml), stirring the mixture at room temperature for one hour, adding a saturated aqueous solution of NH.sub.4 Cl(200 ml) after completion of the reaction, extracting with ethyl acetate (500 ml), drying the organic layer over anhydrous MgSO.sub.4, and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(2'-(4"-hydroxy-4"-(3'",4'",5'"-trifluorophenyl)cycloh exyl)ethylcyclohexane (23.8 g).

(2) p-Toluenesulfonic acidmonohydrate (5 g) was added into a solution of 1,1-ethylenedioxy-4-(2'-(4"-hydroxy-4'"-(3'",4'",5'"-trifluorophenyl)cyclo hexyl)ethyl)cyclohexane (23.8 g) in toluene (250 ml), followed by stirring the mixture under reflux for one hour, washing the reaction solution with water (250 ml), drying the organic layer over anhydrous MgSO.sub.4 and distilling off the solvent under reduced pressure, to obtain 1,1-ethylenedioxy-4-(2'-(4"-(3'",4'",5'"-trifluorophenyl)-3"-cyclohexenyl) ethyl)cyclohexane (18.2 g).

(3) 1,1-Ethylenedioxy-4-(2'-(4"-(3'",4'41 ,5'"-trifluorophenyl)-3"-cyclohexenyl)ethyl)cyclohexane (18.2 g) and DDQ (14.1 g) were dissolved in toluene (250 ml), followed by stirring the mixture under reflux for 4 hours, filtering off deposited insolubles, washing the organic layer with water, drying over anhydrous MgSO.sub.4, distilling off the solvent under reduced pressure, and purifying the resulting raw product according to column chromatography on silica gel (eluent solvent: ethyl acetate/heptane=1/5), to obtain 1,1-ethylenedioxy-4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)cyclohexane (12.6 g).

(4) Formic acid (10 g) and toluene (2 ml) were added to 1,1-ethylenedioxy-4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)cyclohexane (12.6 followed by heating the mixture under reflux with stirring for 2 hours, adding the reaction solution to water (50 ml), extracting with ethyl acetate (50 ml), drying the organic solvent over anhydrous MgSO.sub.4, and distilling off the solvent under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)cyclohexanone (10.0 g).

(5) A suspension of methoxymethyltriphenylphosphonium chloride (11.3 g) in THF (50 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (4.1 g) little by little while cooling at 0.degree. C. stirring the reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)cyclohexanone (10.0 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring the mixture for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (200 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure and carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5), to obtain 4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)methoxymethylenecyclohexane (7.5 g).

(6) THF (50 ml) and 2N hydrochloric acid (50 ml) were added to 4-(2'-(3",4",5"trifluoro-4'"-biphenyl)ethyl)methoxymethylenecyclohexane (7.5 g), followed by heating the mixture under reflux with stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, and concentrating under reduced pressure, to obtain 4-(2'-(3",4",5"-trifluoro-4'"-biphenyl)ethyl)cyclohexylcarbaldehyde (5.8 g).

(7) A suspension of methyltriphenylphosphonium bromide (7.2 g) in THF (20 ml) was stirred in a nitrogen gas stream, followed by adding potassium-t-butoxide (1.6 g) little by little while cooling at 0.degree. C., stirring the resulting reaction solution at room temperature for one hour, dropwise adding a solution of 4-(2'(3",4",5"-trifluoro-4'"-biphenyl)-ethyl)cyclohexanecarbaldehyde (5.8 g) in THF (50 ml), raising the temperature of the reaction mixture up to room temperature, further stirring for 2 hours, adding to water (100 ml) after completion of the reaction, extracting with ethyl acetate (100 ml), drying the organic layer over anhydrous MgSO.sub.4, concentrating under reduced pressure, carrying out chromatography treatment on silica gel with ethyl acetate/heptane (1:5) and recrystallizing from heptane, to obtain 2-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"biphenyl)ethyl)cyclohexyl)ethene (3.5 g).

The following compounds are prepared by repeating the above-mentioned carbon number-increasing reactions:

482. 3-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-1- propene

483. 3-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-2E -propene

484. 4-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-1- butene

485. 4-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-2E -butene

486. 4-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-3E -butene

487. 5-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-1- pentene

488. 5-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-2E -pentene

489. 5-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-3E -pentene

490. 5-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-4E -pentene

491. 6-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-1- hexene

492. 6-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-2E -hexene

493. 6-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-3E -hexene

494. 6-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-4E -hexene

495. 7-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-2E -heptene

496. 7-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-3E -heptene

497. 7-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)-4E-heptene

498. 8-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-3E -octene

499. 8-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-4E -octene

500. 9-(4'-trans-(2"-(3'",4'",5'"-trifluoro-4'"-biphenylyl)ethyl)cyclohexyl)-4E -nonene

501. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)ethene

502. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-2E-propene

503. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-1-propane

504. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)1-butene

505. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-2E-butene

506. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-3E-butene

507. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-1-pentene

508. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-2E-pentene

509. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-3E-pentene

510. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-4E-pentene

511. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-1-hexene

512. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-2E-hexene

513. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-3E-hexene

514. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-4E-hexene

515. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-2E-heptene

516. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-3E-heptene

517. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-4E-heptene

518. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-3E-octene

519. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-4E-octene

520. 9-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethyl-4'"-biphenylyl)ethyl )cyclohexyl)-4E-nonene

521. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)ethene

522. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-2E-propene

523. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-1-propene

524. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-1-butene

525. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-2E -butene

526. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-3E-butene

527. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-1-pentene

528. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-2E-pentene

529. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-3E-pentene

530. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-4E-pentene

531. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-1-hexene

532. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-2E-hexene

533. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-3E-hexene

534. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'-biphenylyl)ethyl )cyclohexyl)-4E-hexene

535. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-2E-heptene

536. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-3E-heptene

537. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-4E-heptene

538. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-3E-octene

539. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'-biphenylyl)ethyl )cyclohexyl)-4E-octene

540. 9-(4'-trans-(2"-(3'",5'"-difluoro-4'"-trifluoromethoxy-4'"-biphenylyl)ethy l)cyclohexyl)-4E-nonene

541. 2-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)ethene

542. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-2E-propene

543. 3-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-1-propene

544. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-1-butene

545. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-2E-butene

546. 4-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-3E-butene

547. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-1-pentene

548. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-2E-pentene

549. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-3E-pentene

550. 5-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-4E-pentene

551. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-1-hexene

552. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-2E-hexene

553. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4 '-biphenylyl)ethyl)cyclohexyl)-3E-hexene

554. 6-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4 '-biphenylyl)ethyl)cyclohexyl)-4E-hexene

555. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-2E-heptene

556. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-3E-heptene

557. 7-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-4E-heptene

558. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-3E-octene

559. 8-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-4E-octene

560. 9-(4'-trans-(2"-(3'",5'"-difluoro-4'"-difluoromethoxy-4'"-biphenylyl)ethyl )cyclohexyl)-4E-nonene

A compound of the present invention (15 parts by weight) shown in Example 1 was added to a composition A consisting of ##STR12##

The resulting liquid crystal composition exhibited an NI point of -95.6.degree. C. when extrapolated, and a viscosity at 20.degree. C. of 2.3 cp. This liquid crystal composition was sealed in a TN cell of 8.7 .mu.m thick, and its threshold voltage was observed to give 1.28 V. Its elastic constant of K.sub.33 /K.sub.11, was 1.99 and that of K.sub.33 /K.sub.22 was 2.69.

As a comparative example, a comparative compound (B) expressed by the formula, ##STR13## (15 parts by weight) was added to the composition (A) (85 parts by weight). The resulting liquid crystal composition exhibited a NI joint of -59.6.degree. C. when extrapolated, and a viscosity at 20.degree. C. of -1.0 cp. Further, this liquid crystal composition was sealed in a TN cell of 8.7 .mu.m thick, and its threshold voltage was observed to give 1.44 V. Its elastic constant of K.sub.33 /K.sub.11 was 1.74 and that of K.sub.33 /K.sub.22 was 2.07.

A compound of the present invention shown in Example 2 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of -119.6.degree. C. when extrapolated. When the composition was filled in a TN cell of 8.7 .mu.m thick and the threshold voltage was observed to give 1.15 V. The elastic constant of K.sub.33 /K.sub.11 was 1.77 and that of K.sub.33 /K.sub.22 was 2.53.

A compound of the present invention shown in Example 4 (15 parts by weight) was added to the composition A used in Application example 1. The resulting liquid crystal composition exhibited an NI point of 57.1.degree. C. and a viscosity at 20.degree. C. of 3.1 cp. This liquid crystal composition was filled in a TN cell of 8.7 .mu.m thick and the threshold voltage was observed to give 1.55 V. The elastic constant of K.sub.33 /K.sub.11 was 2.00 and that of K.sub.33 /K.sub.22 was 2.93.

As a comparative example, a comparative compound (C) expressed by the formula ##STR14## (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The liquid crystal composition exhibited an NI point of 47.7.degree. C. when extrapolated and a viscosity at 20.degree. C. of 30.3 cp. This liquid crystal composition was filled in a TN cell of 8.8 .mu.m thick and the threshold voltage was observed to give 1.48 V, The elastic constant of K.sub.33 /K.sub.11 was 2.11 and that of K.sub.33 /K.sub.22 was 2.86.

A compound of the present invention shown in Example 3 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of -133.6.degree. C. when extrapolated, Further, this liquid crystal composition was filled in a TN cell of 8.7 .mu.m thick and the threshold voltage was observed to give 1.00 V.

A compound of the present invention shown as compound No. 84 (15 parts by weight) was added to the composition A used in Application example 1 (85 parts by weight). The resulting liquid crystal composition exhibited an NI point of 79.1 .degree. C. when extrapolated and a viscosity at 20.degree. C. of 29.0 cp. This liquid crystal composition was filled in a TN cell of 8.6 .mu.m thick and the threshold voltage was observed to give 1.63 V.

The compound provided by the present invention has a low viscosity and when the compound is added, it is possible to lower the threshold voltage of the resulting display element.