US 4,985,583 AGrant

Cyclohexane Derivatives

Issue Date:1991-01-15

•33 Claims

Abstract

New cyclohexane derivatives of the formula I wherein and, if p=2, the groups A.sup.3 can be identical or different, and the acid addition salts of the basic compounds of this type, are suitable for use as components of liquid crystal dielectrics. R.sup.1 and R.sup.2 are each H, an unsubstituted or substituted alkyl group with 1-15 C atoms, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by at least one grouping from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, --SO-- and --SO.sub.2 --, F, Cl, Br, CN or R.sup.3 --(A.sup.3).sub.p --Z.sup.2 --, A.sup.1 is --A--, --A.sup.4 --Z.sup.3 --A-- or --A--Z.sup.3 --A.sup.4 --, A is a 1,4-cyclohexylene group which is substituted in the 1- and/or 4-position by unsubstituted or substituted alkyl or fluorinated alkyl with in each case 1-5 C atoms, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by one grouping from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, --SO-- and --SO.sub.2 --, or by F, Cl, Br, CN and/or --CHO, and which can carry 1 or 2 further substituents, A.sup.2, A.sup.3 and A.sup.4 in each case denote 1,4-phenylene which is unsubstituted or substituted by one or two F and/or Cl atoms and/or CH.sub.3 groups and/or CN groups, it also being possible for one or two CH groups to be replaced by N atoms, 1,4-cyclohexylene, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by O atoms, 1,4-cyclo-1-enyl, 1,3-dithiane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)-octylene, unsubstituted or CN-substituted decahydronaphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl or --A--, Z.sup.1, Z.sup.2 and Z.sup.3 each are --CO--O--, --O--CO--, --OCH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --, substituted ethylene or a single bond, R.sup.3 is H, an unsubstituted or substituted alkyl group with 1-15 C atoms, it also being possible for one or two non-adjacent CH.sub.2 groups to be replaced by a grouping from the group comprising --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, --SO-- and --SO.sub.2 --, F, Cl, Br or CN and p is 1 or 2,

Metadata

Assignee

Merck Patent Gesellschaft mit beschrankter Haftung

Inventors

Rudolf Eidenschink
Joachim Krause
Andreas Wachtler
Reinhard Hittich
Bernhard Scheuble
Georg Weber
Hans-Adolf Kurmeier

Application Information

Application Number:US 0355488

Filing Date:1987-04-07

Priority Date:1982-08-26

Art Unit:223

Classifications

IPC:

C07C25500C09K 1952

Field of Search:

252350558544546299.01;299.5;299.61;299.62;299.63350 R426;431241;242;295;296;298;336;357186;187;189;190;191;192;193;194;255;256;275;276;286;287

Patent Drawings

This patent does not have any drawings.

Description

Example 1

62.5 ml (0.1 mole) of a 1.6M solution of n-butyl-lithium in hexane and 33.1 g (0.1 mole) of 4-(4-cyanocyclohexyl)-4'-pentylbiphenyl (obtainable by Grignard reaction of 4-bromo-4'-pentyl-biphenyl with 4-(4,5-dihydro-4,4-dimethyl-2-oxazolyl)-cyclohexanone (J. Org. Chem. 39 (18), 2787-93 (1974)), detachment of water and simultaneous removal of the oxazolyl protective group by boiling with ethanolic H.sub.2 SO.sub.4, hydrogenation of the double bond and subsequent conversion of the ester into the nitrile) in 40 ml of THF are successively added dropwise to 10.1 g (0.1 mole) of diisopropylamine in 70 ml of THF at -10.degree., with exclusion of moisture and under a nitrogen atmosphere. The reaction mixture is then stirred for 20 minutes. 13.5 g (0.11 mole) of 1-bromopropane are then added, also at -10.degree., and the mixture is subsequently stirred at room temperature for a further 20 minutes. After customary working up, 4-(4-cyano-4-propylcyclohexyl)-4'-pentylbiphenyl is obtained.

The following compounds are prepared analogously:

4-(4-cyano-4-propylcyclohexyl)-4'-ethylbiphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-propylbiphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-butylbiphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-heptylbiphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-ethylbiphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-propylbiphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-butylbiphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-pentylbiphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-heptylbiphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-ethylbiphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-propylbiphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-butylbiphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-pentylbiphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-heptylbiphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-ethylbiphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-propylbiphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-butylbiphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-pentylbiphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-heptylbiphenyl

4-(4-cyano-4-nonylcyclohexyl)-4'-ethylbiphenyl

4-(4-cyano-4-nonylcyclohexyl)-4'-propylbiphenyl

4-(4-cyano-4-nonylcyclohexyl)-4'-butylbiphenyl

4-(4-cyano-4-nonylcyclohexyl)-4'-pentylbiphenyl

4-(4-cyano-4-nonylcyclohexyl)-4'-heptylbiphenyl

Example 2

55 ml of a 1M solution of diisobutyl-aluminium hydride (DIBAH) in n-hexane are added to a solution of 8.6 g (0.05 mole) of 4-(4-cyano-4-propyl-cyclohexyl)-4'-n-pentylbiphenyl (Example 1) in 100 ml of hexane at 0.degree., under a nitrogen atmosphere and with exclusion of moisture. The mixture is stirred at room temperature for one hour and 5 ml of methanol are then carefully added. The reaction mixture is poured into 200 ml of ice-cold 10% H.sub.2 SO.sub.4 and stirred for 30 minutes. The organic phase is then separated off and the aqueous phase is extracted twice more with hexane. The combined organic phases are neutralised with NaHCO.sub.3 solution and then dried. Purification by chromatography gives 4-(4-formyl-4-propylcyclohexyl)-4'-pentylbiphenyl.

The following compounds are prepared analogously:

4-(4-formyl-4-n-propylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-formyl-4-n-propylcyclohexyl)-4'-n-propylbiphenyl

4-(4-formyl-4-n-propylcyclohexyl)-4'-n-butylbiphenyl

4-(4-formyl-4-n-propylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-formyl-4-n-butylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-formyl-4-n-butylcyclohexyl)-4'-n-propylbiphenyl

4-(4-formyl-4-n-butylcyclohexyl)-4'-n-butylbiphenyl

4-(4-formyl-4-n-butylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-formyl-4-n-butylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-formyl-4-n-pentylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-formyl-4-n-pentylcyclohexyl)-4'-n-propylbiphenyl

4-(4-formyl-4-n-pentylcyclohexyl)-4'-n-butylbiphenyl

4-(4-formyl-4-n-pentylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-formyl-4-n-pentylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-formyl-4-n-heptylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-formyl-4-n-heptylcyclohexyl)-4'-n-propylbiphenyl

4-(4-formyl-4-n-heptylcyclohexyl)-4'-n-butylbiphenyl

4-(4-formyl-4-n-heptylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-formyl-4-n-heptylcyclohexyl)-4'-n-heptylbiphenyl

Example 3

A mixture of 3.7 g (0.01 mole) of 4-(4-formyl-4-propylcyclohexyl)-4'-pentylbiphenyl (Example 2), 40 ml of diethylene glycol, 15 ml of 90% hydrazine hydrate and 5.5 g of potassium hydroxide is heated and the hydrazine and water are distilled off until the temperature has risen to about 230.degree. C. The reaction mixture is then boiled for 12 hours and, when cold, 200 ml of water are subsequently added. After customary working up, 4-(4-methyl-4-propylcyclohexyl)-4'-pentylbiphenyl is obtained.

The following compounds are prepared analogously:

4-(4-methyl-4-n-propylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-methyl-4-n-propylcyclohexyl)-4'-n-propylbiphenyl

4-(4-methyl-4-n-propylcyclohexyl)-4'-n-butylbiphenyl

4-(4-methyl-4-n-propylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-methyl-4-n-butylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-methyl-4-n-butylcyclohexyl)-4'-n-propylbiphenyl

4-(4-methyl-4-n-butylcyclohexyl)-4'-n-butylbiphenyl

4-(4-methyl-4-n-butylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-methyl-4-n-butylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-methyl-4-n-pentylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-methyl-4-n-pentylcyclohexyl)-4'-n-propylbiphenyl

4-(4-methyl-4-n-pentylcyclohexyl)-4'-n-butylbiphenyl

4-(4-methyl-4-n-pentylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-methyl-4-n-pentylcyclohexyl)-4'-n-heptylbiphenyl

4-(4-methyl-4-n-heptylcyclohexyl)-4'-n-ethylbiphenyl

4-(4-methyl-4-n-heptylcyclohexyl)-4'-n-propylbiphenyl

4-(4-methyl-4-n-heptylcyclohexyl)-4'-n-butylbiphenyl

4-(4-methyl-4-n-heptylcyclohexyl)-4'-n-pentylbiphenyl

4-(4-methyl-4-n-heptylcyclohexyl)-4'-n-heptylbiphenyl

Example 4

4-(4-Cyano-4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl is obtained from 4-(4-cyanocyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl (obtainable from 4-bromo-4'-(4-pentylcyclohexyl)-biphenyl analogously to Example 1) and 1-bromopropane analogously to Example 1.

The following compounds are prepared analogously:

4-(4-cyano-4-propylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

Example 5

4-(4-Formyl-4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl is obtained from 4-(4-cyano-4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl (Example 4) analogously to Example 2.

The following compounds are prepared analogously:

4-(4-formyl-4-propylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-formyl-4-propylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-formyl-4-propylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-formyl-4-propylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-formyl-4-butylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-formyl-4-butylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-formyl-4-butylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-formyl-4-butylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-formyl-4-butylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-formyl-4-pentylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-formyl-4-pentylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-formyl-4-pentylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-formyl-4-pentylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-formyl-4-pentylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-formyl-4-heptylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-formyl-4-heptylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-formyl-4-heptylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-formyl-4-heptylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-formyl-4-heptylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

Example 6

4-(4-Methyl-4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl is obtained from 4-(4-formyl-4-propylcyclohexyl)-4'-(4-pentylcyclohexyl)-biphenyl (Example 5) analogously to Example 3.

The following compounds are prepared analogously:

4-(4-methyl-4-propylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-methyl-4-propylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-methyl-4-propylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-methyl-4-propylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-methyl-4-butylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-methyl-4-butylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-methyl-4-butylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-methyl-4-butylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-methyl-4-butylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

4-(4-methyl-4-heptylcyclohexyl)-4'-(4-ethylcyclohexyl)biphenyl

4-(4-methyl-4-heptylcyclohexyl)-4'-(4-propylcyclohexyl)biphenyl

4-(4-methyl-4-heptylcyclohexyl)-4'-(4-butylcyclohexyl)biphenyl

4-(4-methyl-4-heptylcyclohexyl)-4'-(4-pentylcyclohexyl)biphenyl

4-(4-methyl-4-heptylcyclohexyl)-4'-(4-heptylcyclohexyl)biphenyl

Example 7

62.5 ml (0.1 mole) of a 1.6M solution of n-butyl-lithium in hexane and 36.5 g (0.1 mole) of 1-(p-(4-cyanocyclohexyl)-phenyl)-2-(trans-4-pentylcyclohexyl)ethane [obtainable by Friedel-Crafts acylation of benzene with trans-4-pentylcyclohexylacetyl chloride, reduction of the carbonyl group by a Wolff-Kishner reaction, bromination of the aromatic ring in the p-position and subsequent Grignard reaction of the resulting 1-(p-bromophenyl)-2-(trans-4-pentylcyclohexyl)-ethane with 4-(4,5-dihydro-4,4-dimethyl-2-oxazoyl)-cyclohexanone, detachment of water, with simultaneous removal of the oxazolyl protective group, by boiling with ethanolic H.sub.2 SO.sub.4, hydrogenation of the double bond and conversion of the ethyl ester into the nitrile] in 50 ml of THF are added dropwise in succession to 10.1 g (0.1 mole) of diisopropylamine in 100 ml of THF at -10.degree. with the exclusion of moisture and under a nitrogen atmosphere. The reaction mixture is stirred for 20 minutes. 16.6 g (0.11 mole) of bromopentane are then added at -10.degree. and the mixture is subsequently stirred at room temperature for a further 20 minutes. After customary working up, 1-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-pentyl-cyclohexyl)eth ane is obtained.

The following compounds are prepared analogously:

1-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan

1-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

1-[p-(4-cyano-4-heptylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan e

1-[p-(4-cyano-4-heptylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-cyano-4-heptylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-cyano-4-heptylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-etha ne

1-[p-(4-cyano-4-heptylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

1-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethane

1-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-ethan e

1-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethane

1-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-ethan e

1-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-ethan e

1-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan e

1-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-etha ne

1-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

1-[p-(4-cyano-4-ethylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethane

1-[p-(4-cyano-4-ethylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-ethan e

1-[p-(4-cyano-4-ethylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethane

1-[p-(4-cyano-4-ethylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-ethan e

1-[p-(4-cyano-4-ethylcyclohexyl)-phenyl]-2-trans-4-heptylcyclohexyl)-ethane

Example 8

1-[p-(4-Formyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-eth ane is obtained from 1-[p-( 4-cyano-4-pentylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-ethane (Example 7) analogously to Example 2.

The following compounds are prepared analogously:

1-[p-(4-formyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-formyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-formyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-formyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

1-[p-(4-formyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-formyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-formyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-formyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-eth ane

1-[p-(4-formyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

1-[p-(4-formyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan e

1-[p-(4-formyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-formyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-formyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-etha ne

1-[p-(4-formyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

1-[p-(4-formyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-formyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-formyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-formyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-eth ane

1-[p-(4-formyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

Example 9

A mixture of 4.4 g (0.01 mole) of 1-[p-(4-formyl4-pentylcyclohexyl)-phenyl]-2-(trans-4-pentyl-cyclohexyl)eth ane (Example 8), 40 ml of diethylene glycol, 15 ml of 90% hydrazine and 5.5 g of potassium hydroxide is heated and the hydrazine and water are distilled off until the temperature has risen to about 230.degree. C. The reaction mixture is then boiled for 12 hours and, when cold, 200 ml of water are subsequently added. After customary working up, 1-[p-(4-methyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-et hane is obtained.

The following compounds are prepared analogously:

1-[p-(4-methyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-methyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-methyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-methyl-4-pentylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

1-[p-(4-methyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-methyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-methyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-methyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-eth ane

1-[p-(4-methyl-4-heptylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

1-[p-(4-methyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan e

1-[p-(4-methyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-methyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-methyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-etha ne

1-[p-(4-methyl-4-butylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

1-[p-(4-methyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-etha ne

1-[p-(4-methyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-eth ane

1-[p-(4-methyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-etha ne

1-[p-(4-methyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-eth ane

1-[p-(4-methyl-4-propylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-eth ane

1-[p-(4-methyl-4-ethylcyclohexyl)-phenyl]-2-(trans-4-ethylcyclohexyl)-ethan e

1-[p-(4-methyl-4-ethylcyclohexyl)-phenyl]-2-(trans-4-propylcyclohexyl)-etha ne

1-[p-(4-methyl-4-ethylcyclohexyl)-phenyl]-2-(trans-4-butylcyclohexyl)-ethan e

1-[p-(4-methyl-4-ethylcyclohexyl)-phenyl]-2-(trans-4-pentylcyclohexyl)-etha ne

1-[p-(4-methyl-4-ethylcyclohexyl)-phenyl]-2-(trans-4-heptylcyclohexyl)-etha ne

Example 10

1 g of 4-dimethylaminopyridine and 30.3 g (0.1 mole) of 4-cyano-4-heptyl-4'-hydroxybicyclohexane (obtainable from 4-(1,4-dioxaspiro[4,5]dec-8-yl)-cyclohexanone by introduction of the nitrile group with tosylmethyl isocyanide (TOSMIC), alkylation with LDA (diisopropylamine/butyl-lithium) and heptyl bromide, detachment of the keto-protective group, reduction of the ketone with NaBH.sub.4 to the alcohol and separation of the isomers) are added to 19.8 g (0.1 mole) of trans-4-pentylcyclohexanecarboxylic acid in 75 ml of CH.sub.2 Cl.sub.2, with stirring. A solution of 27.7 g (0.105 mole) of dicyclo-hexylcarbodiimide in 50 ml of methylene chloride is added dropwise at 0.degree., while controlling the temperature, and the mixture is then stirred at room temperature for a further hour. The urea precipitated is separated off and the methylene chloride phase is washed with dilute HCl and saturated NaHCO.sub.3 solution and dried. The product is then purified by filtration over a short silica gel column and by crystallisation. 4-Cyano-4-heptyl-4'-(trans-4-pentylcyclohexylcarbonyloxy)-bicyclohexane is obtained.

The following compounds are prepared analogously:

4-cyano-4-heptyl-4'-(trans-4-ethylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-heptyl-4'-(trans-4-propylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-heptyl-4'-(trans-4-butylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-heptyl-4'-(trans-4-heptylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-pentyl-4'-(trans-4-ethylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-pentyl-4'-(trans-4-propylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-pentyl-4'-(trans-4-butylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-pentyl-4'-(trans-4-pentylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-pentyl-4'-(trans-4-heptylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-propyl-4'-(trans-4-ethylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-propyl-4'-(trans-4-propylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-propyl-4'-(trans-4-butylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-propyl-4'-(trans-4-pentylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-propyl-4'-(trans-4-heptylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-ethyl-4'-(trans-4-ethylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-ethyl-4'-(trans-4-propylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-ethyl-4'-(trans-4-butylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-ethyl-4'-(trans-4-pentylcyclohexylcarbonyloxy)bicyclohexane

4-cyano-4-ethyl-4'-(trans-4-heptylcyclohexylcarbonyloxy)bicyclohexane

Example 11

1 g of 4-dimethylaminopyridine and 22.3 g (0.1 mole) of 4-cyano-4-propylcyclohexanol (isomer mixture) [obtainable from 1,4-dioxaspiro[4,5]decan-8-one by introduction of the nitrile group with tosylmethyl isocyanide, alkylation with LDA and n-heptyl bromide, detachment of the keto-protective group and reduction of the ketone with NaBH.sub.4 ] are added to 26.6 g (0.1 mole) of 4'-butylbicyclohexane-4-carboxylic acid in 75 ml of CH.sub.2 Cl.sub.2, with stirring. A solution of 21.7 g (0.105 mole) of dicyclohexylcarbodiimide in 50 ml of CH.sub.2 Cl.sub.2 is added dropwise, while controlling the temperature, and the mixture is then stirred at room temperature for a further hour. The urea precipitated is separated off and the methylene chloride phase is washed with dilute HCl and saturated NaHCO.sub.3 solution and dried. After the solvent has been evaporated off, the residue is separated into its constituents by column chromatography (silica gel/petroleum ether (30-70):ether (5:1)). 4-(4-Cyano- 4-heptylcyclohexyloxycarbonyl)-4'-butylbicyclohexane is obtained.

The following compounds are prepared analogously:

4-(4-cyano-4-n-heptylcyclohexyloxycarbonyl)-4'-ethylbicyclohexane

4-(4-cyano-4-n-heptylcyclohexyloxycarbonyl)-4'-propylbicyclohexane

4-(4-cyano-4-n-heptylcyclohexyloxycarbonyl)-4'-pentylbicyclohexane

4-(4-cyano-4-n-heptylcyclohexyloxycarbonyl)-4'-bicyclohexane

4-(4-cyano-4-n-pentylcyclohexyloxycarbonyl)-4'-ethylbicyclohexane

4-(4-cyano-4-n-pentylcyclohexyloxycarbonyl)-4'-propylbicyclohexane

4-(4-cyano-4-n-pentylcyclohexyloxycarbonyl)-4'-butylbicyclohexane

4-(4-cyano-4-n-pentylcyclohexyloxycarbonyl)-4'-pentylbicyclohexane

4-(4-cyano-4-n-pentylcyclohexyloxycarbonyl)-4'-heptylbicyclohexane

4-(4-cyano-4-n-butylcyclohexyloxycarbonyl)-4'-ethylbicyclohexane

4-(4-cyano-4-n-butylcyclohexyloxycarbonyl)-4'-propylbicyclohexane

4-(4-cyano-4-n-butylcyclohexyloxycarbonyl)-4'-butylbicyclohexane

4-(4-cyano-4-n-butylcyclohexyloxycarbonyl)-4'-pentylbicyclohexane

4-(4-cyano-4-n-butylcyclohexyloxycarbonyl)-4'-heptylbicyclohexane

4-(4-cyano-4-n-propylcyclohexyloxycarbonyl)-4'-ethylbicyclohexane

4-(4-cyano-4-n-propylcyclohexyloxycarbonyl)-4'-propylbicyclohexane

4-(4-cyano-4-n-propylcyclohexyloxycarbonyl)-4'-butylbicyclohexane

4-(4-(4-cyano-4-n-propylcyclohexyloxycarbonyl)-4'-pentylbicyclohexane

4-(4-cyano-4-n-propylcyclohexyloxycarbonyl)-4'-heptylbicyclohexane

Example 12

27.2 g (0.1 mole) of p-(4-methyl-4-pentylcyclohexyl)-benzaldehyde (obtainable from 4-cyanocyclohexylbenzene by alkylation with LDA and heptyl bromide, stepwise conversion of the nitrile group into the methyl group by reduction with DIBAH and hydrazine in a Wolff-Kishner reaction and introduction of the formyl group by chloromethylation and a Sommelet reaction) are boiled with 16.0 g (0.1 mole) of 2-hexylpropane-1,3-diol and 0.1 g of p-toluenesulfonic acid in 150 ml of toluene, using a water separator, until no further water of reaction is formed. The cooled reaction mixture is washed twice with 5% NaHCO.sub.3 solution (100 ml each time) and then with water and dried. After the solvent has been evaporated off, the residue is recrystallised from ethanol. p-(4-Methyl-4-pentylcyclohexyl)-(5-hexyl-1,3-dioxan-2-yl)-benzene is obtained.

The following compounds are prepared analogously:

p-(4-methyl-4-pentylcyclohexyl)-(5-ethyl-1,3-dioxan-2-yl)-benzene.

p-(4-methyl-4-pentylcyclohexyl)-(5-propyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-pentylcyclohexyl)-(5-butyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-pentylcyclohexyl)-(5-pentyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-pentylcyclohexyl)-(5-heptyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-propylcyclohexyl)-(5-ethyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-propylcyclohexyl)-(5-propyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-propylcyclohexyl)-(5-butyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-propylcyclohexyl)-(5-pentyl-1,3-dioxan-2-yl)-benzene

p-(4-methyl-4-propylcyclohexyl)-(5-heptyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-pentylcyclohexyl)-(5-ethyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-pentylcyclohexyl)-(5-propyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-pentylcyclohexyl)-(5-butyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-pentylcyclohexyl)-(5-pentyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-pentylcyclohexyl)-(5-heptyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-butylcyclohexyl)-(5-ethyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-butylcyclohexyl)-(5-propyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-butylcyclohexyl)-(5-butyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-butylcyclohexyl)-(5-pentyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-butylcyclohexyl)-(5-heptyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-propylcyclohexyl)-(5-ethyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-propylcyclohexyl)-(5-propyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-propylcyclohexyl)-(5-butyl-1,3-dioxan-2-yl)benzene

p-(4-cyano-4-propylcyclohexyl)-(5-pentyl-1,3-dioxan-2-yl)-benzene

p-(4-cyano-4-propylcyclohexyl)-(5-heptyl-1,3-dioxan-2-yl)-benzene

4-(4-cyano-4-heptylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-heptylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-pentylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-butylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-propylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-ethylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-ethylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-ethylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-ethylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-biphenyl

4-(4-cyano-4-ethylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-biphenyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-2'-fluoro-biph enyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-2'-fluoro-bip henyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-2'-fluoro-biph enyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-2'-fluoro-bip henyl

4-(4-methyl-4-pentylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-2'-fluoro-bip henyl

4-(4-methyl-4-propylcyclohexyl)-4'-(5-ethyl-1,3-dioxan-2-yl)-2-fluoro-biphe nyl

4-(4-methyl-4-propylcyclohexyl)-4'-(5-propyl-1,3-dioxan-2-yl)-2-fluoro-biph enyl

4-(4-methyl-4-propylcyclohexyl)-4'-(5-butyl-1,3-dioxan-2-yl)-2-fluoro-biphe nyl

4-(4-methyl-4-propylcyclohexyl)-4'-(5-pentyl-1,3-dioxan-2-yl)-2-fluoro-biph enyl

4-(4-methyl-4-propylcyclohexyl)-4'-(5-heptyl-1,3-dioxan-2-yl)-2-fluoro-biph enyl

Example 13

An isomer mixture of 1-hydroxy-1-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-4-n-propylcycloh exane [obtainable by reacting 4-n-propylcyclohexanone with 4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl-magnesium bromide and subsequent hydrolysis] is separated into the two stereoisomers by chromatography.

4.5 g of one of these alcohols are dissolved in 50 ml of methylene chloride and the solution is added dropwise to a solution of 1.7 ml of diethylamino-sulfur trifluoride (DAST) and 50 ml of methylene chloride at -60.degree. in the course of 20 minutes. After 5 hours, the mixture is allowed to warm to room temperature and is stirred for 8 hours. After customary working up and recrystallisation from ethyl acetate, 2.2 g of r-1-fluoro-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-trans-4-propylcyc lohexane of m.p. 267.degree. are obtained.

0.3 g of r-1-fluoro-1-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-cis-4-propylcyc lohexane of m.p. 176.degree. and c.p. 309.degree. is obtained in an analogous manner from 2.0 g of the other alcohol.

The following compounds are prepared analogously from the corresponding alcohols (in each case the two stereoisomers):

1-fluoro-1-ethyl-4-(trans-4-pentylcyclohexyl)-bi-phenyl-4-yl]-cyclohexane

1-fluoro-1-propyl-4-[4'-(trans-4-pentylcyclohexyl)-bi-phenyl-4-yl]-cyclohex ane

1-fluoro-1-butyl-4-[4'-(trans-4-pentylcyclohexyl)-bi-phenyl-4-yl]-cyclohexa ne

1-fluoro-1-pentyl-4-[4'-(trans-4-pentylcyclohexyl)-bi-phenyl-4-yl]-cyclohex ane

1-fluoro-1-heptyl-4-[4'-(trans-4-pentylcyclohexyl)-bi-phenyl-4-yl]-cyclohex ane

1-fluoro-1-ethyl-4-[p-trans-4-pentylcyclohexyl)-phenyl]cyclohexane

1-fluoro-1-propyl-4-[p-trans-4-pentylcyclohexyl)-phenyl]cyclohexane

1-fluoro-1-butyl-4-[p-trans-4-pentylcyclohexyl)-phenyl]cyclohexane

1-fluoro-1-pentyl-4-[p-trans-4-pentylcyclohexyl)-phenyl]cyclohexane

1-fluoro-1-heptyl-4-[p-trans-4-pentylcyclohexyl)-phenyl]cyclohexane

1-fluoro-1-[p-(trans-4-pentylcyclohexyl)-phenyl]-4-ethylcyclohexane

1-fluoro-1-[p-(trans-4-pentylcyclohexyl)-phenyl]-4-propylcyclohexane

1-fluoro-1-[p-(trans-4-pentylcyclohexyl)-phenyl]-4-butylcyclohexane

1-fluoro-1-[p-(trans-4-pentylcyclohexyl)-phenyl]-4-pentylcyclohexane

1-fluoro-1-[p-(trans-4-pentylcyclohexyl)-phenyl]-4-heptylcyclohexane

1-fluoro-1-[4'-trans-4-pentylcyclohexyl)-biphenyl-4-yl]4-ethylcyclohexane

1-fluoro-1-[4'-trans-4-pentylcyclohexyl)-biphenyl-4-1]4-propylcyclohexane

1-fluoro-1-[4'-trans-4-pentylcyclohexyl)-biphenyl-4-yl]4-butylcyclohexane

1-fluoro-1-[4'-trans-4-pentylcyclohexyl)-biphenyl-4-yl]4-pentylcyclohexane

1-fluoro-1-[4'-trans-4-pentylcyclohexyl)-biphenyl-4-yl]4-heptylcyclohexane

1-fluoro-1-(4'-propylbiphenyl-4-yl)-4-ethylcyclohexane

1-fluoro-1-(4'-propylbiphenyl-4-yl)-4-propylcyclohexane

1-fluoro-1-(4'-propylbiphenyl-4-yl)-4-butylcyclohexane

1-fluoro-1-(4'-propylbiphenyl-4-yl)-4-pentylcyclohexane

1-fluoro-1-(4'-propylbiphenyl-4-yl)-4-heptylcyclohexane

1-fluoro-1-(4'-cyanobiphenyl-4-yl)-4-ethylcyclohexane

1-fluoro-1-(4'-cyanobiphenyl-4-yl)-4-propylcyclohexane

1-fluoro-1-(4'-cyanobiphenyl-4-yl)-4-butylcyclohexane

1-fluoro-1-(4'-cyanobiphenyl-4-yl)-4-pentylcyclohexane

1-fluoro-1-(4'-cyanobiphenyl-4-yl)-4-heptylcyclohexane

1-fluoro-1-(4'-butoxybiphenyl-4-yl)-4-ethylcyclohexane

1-fluoro-1-(4'-butoxybiphenyl-4-yl)-4-propylcyclohexane

1-fluoro-1-(4'-butoxybiphenyl-4-yl)-4-butylcyclohexane

1-fluoro-1-(4'-butoxybiphenyl-4-yl)-4-pentylcyclohexane

1-fluoro-1-(4'-butoxybiphenyl-4-yl)-4-heptylcyclohexane

1-fluoro-1-ethyl-4-(4'-pentylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-propyl-4-(4'-pentylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-butyl-4-(4'-pentylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-pentyl-4-(4'-pentylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-heptyl-4-(4'-pentylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-ethyl-4-(4'-hexyloxybiphenyl -4-yl)-cyclohexane

1-fluoro-1-propyl-4-(4'-hexyloxybiphenyl-4-yl)-cyclohexane

1-fluoro-1-butyl-4-(4'-hexyloxybiphenyl-4-yl)-cyclohexane

1-fluoro-1-pentyl-4-(4'-hexyloxybiphenyl-4-yl)-cyclohexane

1-fluoro-1-heptyl-4-(4'-hexyloxybiphenyl-4-yl)-cyclohexane

1-fluoro-1-ethyl-4-(4'-propylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-propyl-4-(4'-propylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-butyl-4-(4'-propylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-pentyl-4-(4'-propylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-heptyl-4-(4'-propylbiphenyl-4-yl)-cyclohexane

1-fluoro-1-ethyl-4-(p-pentylphenyl)-cyclohexane

1-fluoro-1-propyl-4-(p-pentylphenyl)-cyclohexane

1-fluoro-1-butyl-4-(p-pentylphenyl)-cyclohexane

1-fluoro-1-pentyl-4-(p-pentylphenyl)-cyclohexane

1-fluoro-1-heptyl-4-(p-pentylphenyl)-cyclohexane

1-fluoro-1-ethyl-4-(p-propylphenyl)-cyclohexane

1-fluoro-1-propyl-4-(p-propylphenyl)-cyclohexane

1-fluoro-1-butyl-4-(p-propylphenyl)-cyclohexane

1-fluoro-1-pentyl-4-(p-propylphenyl)-cyclohexane

1-fluoro-1-heptyl-4-(p-propylphenyl)-cyclohexane

1-fluoro-1-(p-pentylphenyl)-4-ethylcyclohexane

1-fluoro-1-(p-pentylphenyl)-4-propylcyclohexane

1-fluoro-1-(p-pentylphenyl)-4-butylcyclohexane

1-fluoro-1-(p-pentylphenyl)-4-pentylcyclohexane

1-fluoro-1-(p-pentylphenyl)-4-heptylcyclohexane

1-fluoro-1-(p-propylphenyl)-4-ethylcyclohexane

1-fluoro-1-(p-propylphenyl)-4-propylcyclohexane

1-fluoro-1-(p-propylphenyl)-4-butylcyclohexane

1-fluoro-1-(p-propylphenyl)-4-pentylcyclohexane

1-fluoro-1-(p-propylphenyl)-4-heptylcyclohexane

1-fluoro-1-(trans-4-propylcyclohexyl)-4-ethylcyclohexane

1-fluoro-1-(trans-4-propylcyclohexyl)-4-propylcyclohexane

1-fluoro-1-(trans-4-propylcyclohexyl)-4-butylcyclohexane

1-fluoro-1-(trans-4-propylcyclohexyl)-4-pentylcyclohexane

1-fluoro-1-(trans-4-propylcyclohexyl)-4-heptylcyclohexane

1-fluoro-1-(trans-4-cyanocyclohexyl)-4-ethylcyclohexane

1-fluoro-1-(trans-4-cyanocyclohexyl)-4-propylcyclohexane

1-fluoro-1-(trans-4-cyanocyclohexyl)-4-butylcyclohexane

1-fluoro-1-(trans-4-cyanocyclohexyl)-4-pentylcyclohexane

1-fluoro-1-(trans-4-cyanocyclohexyl)-4-heptylcyclohexane

1-fluoro-1-ethyl-4-(trans-4-ethylcyclohexyl)-cyclohexane

1-fluoro-1-propyl-4-(trans-4-ethylcyclohexyl)-cyclohexane

1-fluoro-1-butyl-4-(trans-4-ethylcyclohexyl)-cyclohexane

1-fluoro-1-pentyl-4-(trans-4-ethylcyclohexyl)-cyclohexane

1-fluoro-1-heptyl-4-(trans-4-ethylcyclohexyl)-cyclohexane

1-fluoro-1-ethyl-4-(trans-4-propylcyclohexyl)-cyclohexane

1-fluoro-1-propyl-4-(trans-4-propylcyclohexyl)-cyclohexane

1-fluoro-1-butyl-4-(trans-4-propylcyclohexyl)-cyclohexane

1-fluoro-1-pentyl-4-(trans-4-propylcyclohexyl)-cyclohexane

1-fluoro-1-heptyl-4-(trans-4-propylcyclohexyl)-cyclohexane

1-fluoro-1-ethyl=4-(trans-4-pentylcyclohexyl)-cyclohexane

1-fluoro-1-propyl-4-(trans-4-pentylcyclohexyl)-cyclohexane

1-fluoro-1-butyl-4-(trans-4-pentylcyclohexyl)-cyclohexane

1-fluoro-1-pentyl-4-(trans-4-pentylcyclohexyl)-cyclohexane

1-fluoro-1-heptyl-4-(trans-4-pentylcyclohexyl)-cyclohexane

1-fluoro-1-ethyl-4-(trans-4-heptylcyclohexyl)-cyclohexane

1-fluoro-1-propyl-4-(trans-4-heptylcyclohexyl)-cyclohexane

1-fluoro-1-butyl-4-(trans-4-heptylcyclohexyl)-cyclohexane

1-fluoro-1-pentyl-4-(trans-4-heptylcyclohexyl)-cyclohexane

1-fluoro-1-heptyl-4-(trans-4-heptylcyclohexyl)-cyclohexane

Example 14

125 ml (0.2 mole) of a 1.6N solution of butyllithium in hexane and 53 g (0.2 mole) of methyl 4-transpropylbicyclohexyl-4'-carboxylate in 40 ml of THF are added dropwise in succession to 20.3 g (0.2 mole) of diisopropylamine in 140 ml of THF at a temperature between -10.degree. and -15.degree., with exclusion of moisture and under a nitrogen atmosphere. The reaction mixture is then stirred for 20 minutes. 37.6 g (0.21 mole) of 1-bromoheptane are then added, likewise at -10.degree., and the mixture is subsequently stirred at room temperature for a further two hours. Customary working up gives methyl 4-propyl4'-heptyl-bicyclohexyl-4'-carboxylate of m.p. 49.degree..

The following compounds are prepared analogously:

methyl 4-butyl-4'-heptyl-bicyclohexyl-4'-carboxylate

methyl 4-pentyl-4'-heptyl-bicyclohexyl-4'-carboxylate

methyl 4-heptyl-4'-heptyl-bicyclohexyl-4'-carboxylate

methyl 4-ethyl-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-propyl-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-butyl-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-pentyl-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-heptyl-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylated

propyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

pentyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-propyl-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

pentyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-butyl-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

pentyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-pentyl-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-heptylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-butylcyclohexyl)-ethyl]-4'-heptylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-heptylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-heptylcyclohexyl)-ethyl]-4'-heptylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-pentylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-butylcyclohexyl)-ethyl]-4'-pentylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-pentylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-heptylcyclohexyl)-ethyl]-4'-pentylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

ethyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

propyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

butyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

pentyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

heptyl 4-[2-(trans-4-propylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

methyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

ethyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

propyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

butyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

pentyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

heptyl 4-[2-(trans-4-pentylcyclohexyl)-ethyl]-4'-methylbicyclohexyl-4-carboxylate

methyl 4-(p-propylphenyl)-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-butylphenyl)-4'-pentyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-pentylphenyl)-4'-pentyl-bicyclohexyl-4'carboxylate

methyl 4-(p-heptylphenyl)-4'-pentyl-bicyclohexyl-4'carboxylate

methyl 4-(p-propylphenyl)-4'-heptyl-bicyclohexyl-4'carboxylate

methyl 4-(p-butylphenyl)-4'-heptyl-bicyclohexyl-4'carboxylate

methyl 4-(p-pentylphenyl)-4'-heptyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-heptylphenyl)-4'-heptyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-propylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-(p-propylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-(p-propylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-(p-propylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-(p-propylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-(p-butylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-(p-pentylphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate methyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

ethyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

propyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

butyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

hexyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

heptyl 4-(p-butoxyphenyl)-4'-methyl-bicyclohexyl-4'-carboxylate

methyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]1-heptyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-butylcyclohexyl)-biphenyl-4-yl]-1-heptyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-1-heptyl-cyclohexane-1-car boxylate

methyl 4-[4'-(trans-4-heptylcyclohexyl)-biphenyl-4-yl]-1-heptyl-cyclohexane-1-car boxylate

methyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]-1-pentyl-cyclohexane-1-car boxylate

1 methyl 4-[4'-(trans-4-butylcyclohexyl)-biphenyl-4-yl]-1-pentyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]1-pentyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-heptylcyclohexyl)-biphenyl-4-yl]1-pentyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

ethyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]-1-methyl-cyclohexane-1-car boxylate

propyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

butyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]-1-methyl-cyclohexane-1-car boxylate

pentyl 4-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

methyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

ethyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-11methyl-cyclohexane-1-car boxylate

propyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-methyl-cyclohexane-1-carbo xylate

butyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

pentyl 4-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]1-methyl-cyclohexane-1-carb oxylate

Example 15

7.2 g of ethanethiol and 35 g of 4-pentyl-4'heptyl-4'-hydroxybicyclohexane in 70 ml of glacial acetic acid are added dropwise to a mixture of 30 ml of glacial acetic acid, 11.1 g of acetic anhydride and 7 g of 72% aqueous perchloric acid solution at -20.degree.. The mixture is stirred at room temperature for 24 hours, poured into 250 ml of saturated sodium chloride solution, extracted with petroleum ether and worked up in the customary manner. 4-Pentyl-4'-heptyl-4'-ethylthiobicyclohexane is obtained.

The following compounds are prepared analogously:

4-pentyl-4'-propyl-4'-ethylthiobicyclohexane

4-pentyl-4'-butyl-4'-ethylthiobicyclohexane

4-pentyl-4'-pentyl-4'-ethylthiobicyclohexane

4-pentyl-4'-hexyl-4'-ethylthiobicyclohexane

4-pentyl-4'-octyl-4'-ethylthiobicyclohexane

4-propyl-4'-propyl-4'-methylthiobicyclohexane

4-propyl-4'-butyl-4'-methylthiobicyclohexane

4-propyl-4'-pentyl-4'-methylthiobicyclohexane

4-propyl-4'-hexyl-4'-methylthiobicyclohexane

4-propyl-4'-heptyl-4'-methylthiobicyclohexane

4-butyl-4'-propyl-4'-methylthiobicyclohexane

4-butyl-4'-butyl-4'-methylthiobicyclohexane

4-butyl-4'-pentyl-4'-methylthiobicyclohexane

4-butyl-4'-hexyl-4'-methylthiobicyclohexane

4-butyl-4'-heptyl-4'-methylthiobicyclohexane

4-pentyl-4'-propyl-4'-methylthiobicyclohexane

4-pentyl-4'-butyl-4'-methylthiobicyclohexane

4-pentyl-4'-pentyl-4'-methylthiobicyclohexane

4-pentyl-4'-hexyl-4'-methylthiobicyclohexane

4-pentyl-4'-heptyl-4'-methylthiobicyclohexane

4-heptyl-4'-propyl-4'-methylthiobicyclohexane

4-heptyl-4'-butyl-4'-methylthiobicyclohexane

4-heptyl-4'-pentyl-4'-methylthiobicyclohexane

4-heptyl-4'-hexyl-4'-methylthiobicyclohexane

4-heptyl-4'-heptyl-4'-methylthiobicyclohexane

4-pentyl-4'-methyl-4'-ethylthiobicyclohexane

4-pentyl-4'-methyl-4'-propylthiobicyclohexane

4-pentyl-4'-methyl-4'-butylthiobicyclohexane

4-pentyl-4'-methyl-4'-pentylthiobicyclohexane

4-pentyl-4'-methyl-4'-hexylthiobicyclohexane

4-propyl-4'-methyl-4'-ethylthiobicyclohexane

4-propyl-4'-methyl-4'-propylthiobicyclohexane

4-propyl-4'-methyl-4'-butylthiobicyclohexane

4-propyl-4'-methyl-4''-pentylthiobicyclohexane

4-propyl-4'-methyl-4'-hexylthiobicyclohexane

Example 16

3.3 g of 4-pentyl-4'-heptyl-4'-ethylthiobicyclohexane are dissolved in 20 ml of chloroform. A solution of 5.3 g of 70% m-chloroperbenzoic acid in 100 ml of chloroform is added dropwise at 5.degree.-10.degree.. After the mixture has been left to stand for 15 hours and after customary working up, 4-pentyl-4'-heptyl-4'-ethylsulfonylbicyclohexane is obtained.

The following compounds are prepared analogously: 4-pentyl-4'-propyl-4'-ethylsulfonylbicyclohexane

4-pentyl-4'-butyl-4'-ethylsulfonylbicyclohexane

4-pentyl-4'-pentyl-4'-ethylsulfonylbicyclohexane

4-pentyl-4'-hexyl-4'-ethylsulfonylbicyclohexane

4-pentyl-4'-octyl-4'-ethylsulfonylbicyclohexane

4-propyl-4'-propyl-4'-methylsulfonylbicyclohexane

4-propyl-4'-butyl-4'-methylsulfonylbicyclohexane

4-propyl-4,-pentyl-4'-methylsulfonylbicyclohexane

4-propyl-4'-hexyl-4'-methylsulfonylbicyclohexane

4-propyl-4'-heptyl-4'-methylsulfonylbicyclohexane

4-butyl-4'-propyl--4'-methylsulfonylbicyclohexane

4-butyl-4'-butyl-4'-methylsulfonylbicyclohexane

4-butyl-4'-pentyl-4'-methylsulfonylbicyclohexane

4-butyl-4'-hexyl-4'-methylsulfonylbicyclohexane

4-butyl-4'-heptyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-propyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-butyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-pentyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-hexyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-heptyl-4'-methylsulfonylbicyclohexane

4-heptyl-4'-propyl-4'-methylsulfonylbicyclohexane

4-heptyl-4'-butyl-4'-methylsulfonylbicyclohexane

4-heptyl-4'-pentyl-4'-methylsulfonylbicyclohexane

4-heptyl-4'-hexyl-4'-methylsulfonylbicyclohexane

4-heptyl-4'-heptyl-4'-methylsulfonylbicyclohexane

4-pentyl-4'-methyl-4'-ethylsulfonylbicyclohexane

4-pentyl-4'-methyl-4'-propylsulfonylbicyclohexane

4-pentyl-4'-methyl-4'-butylsulfonylbicyclohexane

-pentyl-4'-methyl-4'-pentylsulfonylbicyclohexane

-pentyl-4'-methyl-4'-hexylsulfonylbicyclohexane

-propyl-4'-methyl-4'-ethylsulfonylbicyclohexane

-propyl-4'-methyl-4'-propylsulfonylbicyclohexane

-propyl-4'-methyl-4'-butylsulfonylbicyclohexane

-propyl-4'-methyl-4'-pentylsulfonylbicyclohexane

-propyl-4'-methyl-4'-hexylsulfonylbicyclohexane

Example 17

1 ml of 30% H.sub.2 O.sub.2 is added to 3.8 g of 4-pentyl-4'-heptyl-4'-ethylthiobicyclohexane in 25 ml of glacial acetic acid and the mixture is stirred at room temperature for 3 hours. After customary working up, 4-pentyl-4'-heptyl-4'-ethylsulfinylbicyclohexane is obtained.

The following compounds are prepared analogously:

4-pentyl-4'-propyl-4'-ethylsulfinylbicyclohexane

4-pentyl-4'-butyl-4'-ethylsulfinylbicyclohexane

4-pentyl-4'-pentyl-4'-ethylsulfinylbicyclohexane

4-pentyl-4'-hexyl-4'-ethylsulfinylbicyclohexane

4-pentyl-4'-octyl-4'-ethylsulfinylbicyclohexane

4-propyl-4'-propyl-4'-methylsulfinylbicyclohexane

4-propyl-4'-butyl-4'-methylsulfinylbicyclohexane

4-propyl-4'-pentyl-4'-methylsulfinylbicyclohexane

4-propyl-4'-hexyl-4'-methylsulfinylbicyclohexane

4-propyl-4'-heptyl-4'-methylsulfinylbicyclohexane

4-butyl-4'-propyl-4'-methylsulfinylbicyclohexane

4-butyl-4'-butyl-4'-methylsulfinylbicyclohexane

4-butyl-4'-pentyl-4'-methylsulfinylbicyclohexane

4-butyl-4'-hexyl-4'-methylsulfinylbicyclohexane

4-butyl-4'-heptyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-propyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-butyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-pentyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-hexyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-heptyl-4'-methylsulfinylbicyclohexane

4-heptyl-4'-propyl-4'-methylsulfinylbicyclohexane

4-heptyl-4'-butyl-4'-methylsulfinylbicyclohexane

4-heptyl-4'-pentyl-4'-methylsulfinylbicyclohexane

4-heptyl-4'-hexyl-4'-methylsulfinylbicyclohexane

4-heptyl-4'-heptyl-4'-methylsulfinylbicyclohexane

4-pentyl-4'-methyl-4'-ethylsulfinylbicyclohexane

4-pentyl-4'-methyl-4'-propylsulfinylbicyclohexane

4-pentyl-4'-methyl-4'-butylsulfinylbicyclohexane

4-pentyl-4'-methyl-4'-pentylsulfinylbicyclohexane

4-pentyl-4'-methyl-4'-hexylsulfinylbicyclohexane

4-propyl-4'-methyl-4'-ethylsulfinylbicyclohexane

4-propyl-4'-methyl-4'-propylsulfinylbicyclohexane

4-propyl-4'-methyl-4'-butylsulfinylbicyclohexane

4-propyl-4'-methyl-4'-pentylsulfinylbicyclohexane

4-propyl-4'-methyl-4'-hexylsulfinylbicyclohexane

Example 18

16.4 g of 2-butylpropane-1,3-dithiol, 20.7 g of

4-cyano-4-pentylcyclohexanecarbaldehyde [obtainable by a Wittig reaction from 4-cyano-4-pentylcyclohexanone with triphenylphosphine-toluyloxymethylene and subsequent hydrolysis], 200 ml of methylene chloride and 150 mg of AlCl.sub.3 are stirred for 15 hours. Customary working up gives 2-(4-cyano-4-pentylcyclohexyl)-5-butyl-1,3-dithiane.

The following compounds are prepared analogously:

2-(4-cyano-4-pentylcyclohexyl)-5-ethyl-1,3-dithiane

2-(4-cyano-4-pentylcyclohexyl)-5-propyl-1,3-dithiane

2-(4-cyano-4-pentylcyclohexyl)-5-pentyl-1,3-dithiane

2-(4-cyano-4-pentylcyclohexyl)-5-heptyl-1,3-dithiane

2-(4-cyano-4-heptylcyclohexyl)-5-ethyl-1,3-dithiane

2-(4-cyano-4-heptylcyclohexyl)-5-propyl-1,3-dithiane

2-(4-cyano-4-heptylcyclohexyl)-5-butyl-1,3-dithiane

2-(4-cyano-4-heptylcyclohexyl)-5-pentyl-1,3-dithianze

2-(4-cyano-4-heptylcyclohexyl)-5-heptyl-1,3-dithiane

2-(4-cyano-4-propylcyclohexyl)-5-ethyl-1,3-dithiane

2-(4-cyano-4-propylcyclohexyl)-5-propyl-1,3-dithiane

2-(4-cyano-4-propylcyclohexyl)-5-butyl-1,3-dithiane

2-(4-cyano-4-propylcyclohexyl)-5-pentyl-1,3-dithiane

2-(4-cyano-4-propylcyclohexyl)-5-heptyl-1,3-dithiane

2-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-5-ethyl-1,3-dithiane

2-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-5-propyl-1,3-dithiane

2-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-5-butyl-1,3-dithiane

2-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-5-pentyl-1,3-dithiane

2-[p-(4-cyano-4-propylcyclohexyl)-phenyl]-5-heptyl-1,3-dithiane

2-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-5-ethyl-1,3-dithiane

2-[p-(4--cyano-4-butylcyclohexyl)-phenyl]-5-propyl-1,3-dithiane

2-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-5-butyl-1,3-dithiane

2-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-5-pentyl-3-dithiane

2-[p-(4-cyano-4-butylcyclohexyl)-phenyl]-5-heptyl-1,3-dithiane

2-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-5-ethyl-1,3-dithiane

2-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-5-propyl-1,3-dithiane

2-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-5-butyl-1,3-dithiane

2-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-5-pentyl-1,3-dithiane

2-[p-(4-cyano-4-pentylcyclohexyl)-phenyl]-5-heptyl-1,3-dithiane

2-[4-(4-cyano-4-propylcyclohexyl)-biphenyl-4'-yl]-5-ethyl-1,3-dithiane

2-[4-(4-cyano-4-propylcyclohexyl)-biphenyl-4'-yl]-5-propyl-1,3-dithiane

2-[4-(4-cyano-4-propylcyclohexyl)-biphenyl-4'-yl]-5-butyl-1,3-dithiane

2-[4-(4-cyano-4-propylcyclohexyl)-biphenyl-4'-yl]-5-pentyl-1,3-dithiane

2-[4-(4-cyano-4-propylcyclohexyl)-biphenyl-4'-yl]-5-heptyl-1,3-dithiane

2-[4-(4-cyano-4-butylcyclohexyl)-biphenyl-4'-yl]-5-ethyl-1,3-dithiane

2-[4-(4-cyano-4-butylcyclohexyl)-biphenyl-4'-yl]-5-propyl-1,3-dithiane

2-[4-(4-cyano-4-butylcyclohexyl)-biphenyl-4'-yl]-5-butyl-1,3-dithiane

2-[4-(4-cyano-4-butylcyclohexyl)-biphenyl-4'-yl]-5-pentyl-1,3-dithiane

2-[4-(4-cyano-4-butylcyclohexyl)-biphenyl-4'-yl]-5-heptyl-1,3-dithiane

2-[4-(4-cyano-4-pentylcyclohexyl)-biphenyl-4'-yl]-5-ethyl-1,3-dithiane

2-[4-(4-cyano-4-pentylcyclohexyl)-biphenyl-4'-yl]-5-propyl-1,3-dithiane

2-[4-(4-cyano-4-pentylcyclohexyl)-biphenyl-4'-yl]-5-butyl-1,3-dithiane

2-[4-(4-cyano-4-pentylcyclohexyl)-biphenyl-4'-yl]-5-pentyl-1,3-dithiane

2-[4-(4-cyano-4-pentylcyclohexyl)-biphenyl-4'-yl]-5-heptyl-1,3-dithiane

2-[4-(4-cyano-4-heptylcyclohexyl)-biphenyl-4'-yl]-5-ethyl1,3-dithiane

2-[4-(4-cyano-4-heptylcyclohexyl)-biphenyl-4'-yl]-5-propyl-1,3-dithiane

2-[4-(4-cyano-4-heptylcyclohexyl)-biphenyl-4'-yl]-5-butyl-1,3-dithiane

2-[4-(4-cyano-4-heptylcyclohexyl)-biphenyl-4'-yl]-5-pentyl-1,3-dithiane

2-[4-(-4-cyano-4-heptylcyclohexyl)-biphenyl-4'-yl]-5-heptyl-1,3-dithiane

Example 19

62.5 ml of a 1.6 molar solution of n-butyllithium in hexane and 28.7 g of (4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyanocyclohex yl)-naphthalene [obtainable by a process analogous to those described in German Offenlegungsschrift 3,150,312] in 40 ml of THF are added dropwise in succession to 10.1 g of diisopropylamine in 70 ml of tetrahydrofuran at -10.degree., under a nitrogen atmosphere. The reaction mixture is stirred for 20 minutes. 16.6 g of 1-bromopentane are then added at -10.degree. and the mixture is stirred at room temperature for 20 minutes and worked up in the customary manner to give (4a.alpha.H,8a.beta.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-pentyl )-naphthalene.

The following compounds are prepared analogously:

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-ethyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-propyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-butyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-hexyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-heptyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-propyl-2.alpha.-(4-cyano-4-nonyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-ethyl)n aphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-propyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-butyl)n aphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-hexyl)n aphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-heptyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butyl-2.alpha.-(4-cyano-4-nonyl)n aphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-ethyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-propyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-butyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-hexyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-heptyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-pentyl-2.alpha.-(4-cyano-4-nonyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-ethyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-propyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-butyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-hexyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-heptyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-heptyl-2.alpha.-(4-cyano-4-nonyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-ethyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-propyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-butyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-hexyl) naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-heptyl )naphthalene

(4a.alpha.H,8a.alpha.H)-decahydro-6.beta.-butoxy-2.alpha.-(4-cyano-4-nonyl) naphthalene

Example 20

4.3 g of NaNH.sub.2 (50% in toluene) are added to a solution of 31.5 g of trans,trans,trans-4-cyano-4"-propyltercyclohexyl and 41 g of butylbromide in 70 ml of toluene. The reaction mixture is then boiled for 5 hours. After customary working up, r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cy clohexane is obtained.

The following compounds are prepared analogously by alkylation of corresponding nitriles:

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-propyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-pentyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-heptyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-octyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-nonyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cyclo hexane

r-1-cyano-1-propyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cyclo hexane

r-1-cyano-1-pentyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-heptyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cyclo hexane

r-1-cyano-1-propyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cyclo hexane

r-1-cyano-1-pentyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-heptyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-propyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-pentyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-heptyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-propyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)cyclohexyl]-cycl ohexane

r-1-cyano-1-pentyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-heptyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)cyclohexyl]-cyc lohexane

r-1-cyano-1-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cis-4-ethylcyclo hexane

r-1-cyano-1-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cis-4-propylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cis-4-butylcyclo hexane

r-1-cyano-1-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cis-4-pentylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cis-4-heptylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cis-4-ethylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cis-4-propylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cis-4-butylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cis-4-pentylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cis-4-heptylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cis-4-ethylcyclo hexane

r-1-cyano-1-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cis-4-propylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cis-4-butylcyclo hexane

r-1-cyano-1-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cis-4-pentylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cis-4-heptylcycl ohexane

r-1-cyano-1-trans-4-(trans-4 -pentylcyclohexyl)-cyclohexyl]-cis-4-ethylcyclohexane

r-1-cyano-1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cis-4-propylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cis-4-butylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cis-4-pentylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cis-4-heptylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cis-4-ethylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cis-4-propylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cis-4-butylcycl ohexane

r-1-cyano-1-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cis-4-pentylcyc lohexane

r-1-cyano-1-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cis-4-heptylcyc lohexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-ethylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-propylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-butylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cyc lohexane, m.p. 61.degree., c.p. 198.degree.

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cyc lohexane, m.p. 33.degree., c.p. 199.degree.

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cyc lohexane, m.p. 44.degree., c.p. 192.degree.

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-hexylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-heptylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane, m.p. 60.degree., c.p. 187,5.degree.

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyclo hexane

r-1-cyano-1-(trans-4-octylcyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans4-propylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cy clohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-methoxycyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cy clohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-ethoxycyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cy clohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cy clohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-propoxycyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cy clohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-ethylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-propylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-butylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cyc lohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-hexylcyclohexyl)-cycl ohexane

r-1-cyano-1-(trans-4-butoxycyclohexyl)-cis-4-(trans-4-heptylcyclohexyl)-cyc lohexane

r-1-cyano-1-ethyl-cis-4-[p-(trans-4-propylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-propyl-cis-4-[p-(trans-4-propylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-butyl-cis-4-[p-(trans-4-propylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-pentyl-cis-4-[p-(trans-4-propylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-heptyl-cis-4-[p-(trans-4-propylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-ethyl-cis-4-[p-(trans-4-butylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-propyl-cis-4-[p-(trans-4-butylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-butyl-cis-4-[p-(trans-4-butylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-pentyl-cis-4-[p-(trans-4-butylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-heptyl-cis-4-[p-(trans-4-butylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-ethyl-cis-4-[p-(trans-4-pentylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-propyl-cis-4-[p-(trans-4-pentylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-butyl-cis-4-[p-(trans-4-pentylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-pentyl-cis-4-[p-(trans-4-pentylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-heptyl-cis-4-[p-(trans-4-pentylcyclohexyl)phenyl]-cyclohexane

r-1-cyano-1-propyl-cis-4-[4-(trans-4-propylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

r-1-cyano-1-butyl-cis-4-[4-(trans-4-propylcyclohexyl)biphenyl-4'-yl-cyclohe xane

r-1-cyano-1-pentyl-cis-4-[4-(trans-4-propylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

r-1-cyano-1-heptyl-cis-4-[4-(trans-4-propylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

r-1-cyano-1-ethyl-cis-4-[4-(trans-4-pentylcyclohexyl)biphenyl-4'-yl]-cycloh exane

r-1-cyano-1-propyl-cis-4-[4-(trans-4-pentylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

r-1-cyano-1-butyl-cis-4-[4-(trans-4-pentylcyclohexyl)biphenyl-4'-yl]-cycloh exane

r-1-cyano-1-pentyl-cis-4-[4-(trans-4-pentylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

r-1-cyano-1-heptyl-cis-4-[4-(trans-4-pentylcyclohexyl)biphenyl-4'-yl]-cyclo hexane

Example 21

6 g of NaH (50% in paraffin) are added under stirring to a solution of 26.3 g of 4'-pentyl-biphenylyl-4-acetonitrile [m.p. 80.degree., c.p. -10.degree.; obtainable from 4-acetyl-4'-pentyl-biphenyl by 4'-pentyl-biphenylylacetic acid (m.p. 160.degree.) and the corresponding amide (m.p. 185.degree.)/in 150 ml of dimethylsulfoxide.

Subsequently a solution of 30 g of 1-bromo-3-(2-bromoethyl)-n-hexane in 50 ml of dioxane is added, whereas the temperature is kept under 35.degree. by cooling. The mixture is stirred for 2 hours and, after addition of isopropanol, worked up as customary. r-1-cyano-1-(4'-pentyl-4-biphenylyl)-cis-4-propylcyclohexane is obtained.

The following compounds are prepared analogously from the corresponding acetonitriles and the corresponding dibromides:

r-1-cyano-1-(4'-pentyl-4-biphenylyl)-cis-4-ethylcyclohexane

r-1-cyano-1-(4'-pentyl-4-biphenylyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4'-pentyl-4-biphenylyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4'-pentyl-4-biphenylyl)-cis-4-heptylcyclohexane

r-1-cyano-1-(4'-propyl-4-biphenylyl)-cis-4-ethylcyclohexane

r-1-cyano-1-(4'-propyl-4-biphenylyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4'-propyl-4-biphenylyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4'-propyl-4-biphenylyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4'-propyl-4-biphenylyl)-cis-4-heptylcyclohexane

r-1-cyano-1-(4'-butyl-4-biphenylyl)-cis-4-ethylcyclohexane

r-1-cyano-1-(4'-butyl-4-biphenylyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4'-butyl-4-biphenylyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4'-butyl-4-biphenylyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4'-butyl-4-biphenylyl)-cis-4-heptylcyclohexane

r-1-cyano-1-(4'-heptyl-4-biphenylyl)-cis-4-ethylcyclohexane

r-1-cyano-1-(4'-heptyl-4-biphenylyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4'-heptyl-4-biphenylyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4'-heptyl-4-biphenylyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4'-heptyl-4-biphenylyl)-cis-4-heptylcyclohexane

r-1-cyano-1-(p-ethylphenyl)-cis-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-(p-ethylphenyl)-cis-4-(trans-4-propylcyclohexyl)cyclohexane

r-1-cyano-1-(p-ethylphenyl)-cis-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-(p-ethylphenyl)-cis-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-(p-ethylphenyl)-cis-4-(trans-4-heptylcyclohexyl)cyclohexane

r-1-cyano-1-(p-propylphenyl)-cis-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-(p-propylphenyl)-cis-4-(trans-4-propylcyclohexyl)cyclohexane

r-1-cyano-1-(p-propylphenyl)-cis-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-(p-propylphenyl)-cis-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-(p-propylphenyl)-cis-4-(trans-4-heptylcyclohexyl)cyclohexane

r-1-cyano-1-(p-butylphenyl)-cis-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-(p-butylphenyl)-cis-4-(trans-4-propylcyclohexyl)cyclohexane

r-1-cyano-1-(p-butylphenyl)-cis-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-(p-butylphenyl)-cis-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-(p-butylphenyl)-cis-4-(trans-4-heptylcyclohexyl)cyclohexane

r-1-cyano-1-(p-pentylphenyl)-cis-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-(p-pentylphenyl)-cis-4-(trans-4-propylcyclohexyl)cyclohexane

r-1-cyano-1-(p-pentylphenyl)-cis-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-(p-pentylphenyl)-cis-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-(p-pentylphenyl)-cis-4-(trans-4-heptylcyclohexyl)cyclohexane

r-1-cyano-1-(p-heptylphenyl)-cis-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-(p-heptylphenyl)-cis-4-(trans-4-propylcyclohexyl)cyclohexane

r-1-cyano-1-(p-heptylphenyl)-cis-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-(p-heptylphenyl)-cis-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-(p-heptylphenyl)-cis-4-(trans-4-heptylcyclohexyl)cyclohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-(trans-4-ethylcyclohexyl)-cycloh exane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-(trans-4-propylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-(trans-4-butylcyclohexyl)-cycloh exane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-(trans-4-ethylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-(trans-4-propylcyclohexyl)-cycl ohexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-(trans-4-butylcyclohexyl)-cyclo hexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-(trans-4-pentylcyclohexyl)-cycl ohexane, m.p. 34.degree., c.p. 137.degree.

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-(trans-4-heptylcyclohexyl)-cycl ohexane, m.p. 30.degree., c.p. 133.degree.

r-1-cyano-1-[4-(trans-4-propylcyclohexyl)-cyclohex-1-enyl)cis-4-ethylcycloh exane

r-1-cyano-1-[4-(trans-4-propylcyclohexyl)-cyclohex-1-enyl)cis-4-propylcyclo hexane

r-1-cyano-1-[4-(trans-4-propylcyclohexyl)-cyclohex-1-enyl)cis-4-butylcycloh exane

r-1-cyano-1-[4-(trans-4-propylcyclohexyl)-cyclohex-1-enyl)cis-4-pentylcyclo hexane

r-1-cyano-1-[4-(trans-4-propylcyclohexyl)-cyclohex-1-enyl)cis-4-heptylcyclo hexane

r-1-cyano-1-[4-(trans-4-butylcyclohexyl)-cyclohex-1-enyl)cis-4-ethylcyclohe xane

r-1-cyano-1-[4-(trans-4-butylcyclohexyl)-cyclohex-1-enyl)cis-4-propylcycloh exane

r-1-cyano-1-[4-(trans-4-butylcyclohexyl)-cyclohex-1-enyl)cis-4-butylcyclohe xane

r-1-cyano-1-[4-(trans-4-butylcyclohexyl)-cyclohex-1-enyl)cis-4-pentylcycloh exane

r-1-cyano-1-[4-(trans-4-butylcyclohexyl)-cyclohex-1-enyl)cis-4-heptylcycloh exane

r-1-cyano-1-[4-(trans-4-pentylcyclohexyl)-cyclohex-1-enyl)cis-4-ethylcycloh exane

r-1-cyano-1-[4-(trans-4-pentylcyclohexyl)-cyclohex-1-enyl)cis-4-propylcyclo hexane

r-1-cyano-1-[4-(trans-4-pentylcyclohexyl)-cyclohex-1-enyl)cis-4-butylcycloh exane

r-1-cyano-1-[4-(trans-4-pentylcyclohexyl)-cyclohex-1-enyl)cis-4-pentylcyclo hexane

r-1-cyano-1-[4-(trans-4-pentylcyclohexyl)-cyclohex-1-enyl)cis-4-heptylcyclo hexane

r-1-cyano-1-(4-ethylcyclohex-1-enyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4-heptylcyclohex-1-enyl)-cis-4-propylcyclohexane

r-1-cyano-1-(4-ethylcyclohex-1-enyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4-heptylcyclohex-1-enyl)-cis-4-butylcyclohexane

r-1-cyano-1-(4-ethylcyclohex-1-enyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4-propylcyclohex-1-enyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4-butylcyclohex-1-enyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4-pentylcyclohex-1-enyl)-cis-4-pentylcyclohexane

r-1-cyano-1-(4-heptylcyclohex-1-enyl)-cis-4-pentylcyclohexane

Example 22

26 g of phosphorus oxytrichloride are added dropwise, at 50.degree. C., to a solution of 12.1 g of p-[trans-4-(trans-4-n-pentyl-4-methylcyclohexyl)-cyclohexyl]-benzamide [obtainable from 4-n-pentyl-4-methylcyclohexanone by reaction with a Grignard solution obtained from p-bromoanisole, elimination of water, hydrogenation of the resulting double bond, cleavage of the ether, hydrogenation of the aromatic ring, dehydrogenation to give the cyclohexanone, reaction with phenyl magnesium bromide, elimination of water, hydrogenation of the resulting double bond, Friedel-Crafts acylation with acetyl chloride/AlCl.sub.3, haloform degradation of the resulting acetophenone to give p-[trans-4-(trans-4-n-pentyl-4-methylcyclohexyl)-cyclohexyl]-benzoic acid and conversion to its amide] in 100 ml of dimethylformamide. After 1 hour, the reaction mixture is worked up in the customary manner. p-[trans-(trans-4-n-Pentyl-4-methylcyclohexyl)cyclohexyl]-benzonitrile is obtained.

The following compounds are obtained in an analogous manner: p0 p-[trans-4-(trans-4-hexyl-4-methylcyclohexyl)-cyclohexyl]benzonitrile p0 p-[trans-4-(trans-4-heptyl-4-methylcyclohexyl)-cyclohexyl]-benzonitrile p0 p-[trans-4-(trans-4-butyl-4-methylcyclohexyl)-cyclohexyl]benzonitrile p0 p-[trans-4-(trans-4-propyl-4-methylcyclohexyl)-cyclohexyl]-benzonitrile

p-[trans-4-(trans-4-ethyl-4-methylcyclohexyl)-cyclohexyl]benzonitrile

Example 23

A solution of 2.7 g of 4-cyano-3-fluorophenol and 5 ml of pyridine in 30 ml of toluene is added dropwise to a solution of 6.1 g of p-(4-methyl-4-n-pentylcyclohexyl)benzoyl chloride [obtainable by reaction of the enamine, obtainable from 2-methylheptanal and pyrrolidine, with methyl vinyl ketone according to G. Otani and S. Yamada, Chem. Pharm. Bull. 21(10), 2112-2118 (1973), hydrogenation of the resulting 4-methyl-4-pentyl-2-cyclohexanone to give 4-methyl-4-pentylcyclohexanone (an intermediate of the formula (A)), reaction With phenyl magnesium bromide, hydrolysis and hydrogenation to 4-methyl-4-n-pentylcyclohexylbenzene, reaction with acetyl chloride in the presence of aluminium chloride, subsequent haloform degradation of the resulting acetophenone to give the corresponding benzoic acid and conversion to the acid chloride] in 40 ml of toluene, and the mixture is boiled for 2 hours. After the customary working-up, 4-cyano-3-fluorophenyl p-(4-methyl-4-n-pentylcyclohexyl)benzoate is obtained.

The following compounds are prepared in an analogous manner:

4-cyano-3-fluorophenyl p-(4-methyl-4-ethylcyclohexyl)benzoate

4-cyano-3-fluorophenyl p-(4-methyl-4-propylcyclohexyl)benzoate

4-cyano-3-fluorophenyl p-(4-methyl-4-butylcyclohexyl)benzoate

4-cyano-3-fluorophenyl p-(4-methyl-4-hexylcyclohexyl)benzoate

4-cyano-3-fluorophenyl p-(4-methyl-4-heptylcyclohexyl)benzoate.

Example 24

62,5 ml of butyllithium dissolved in hexane (1,6 m) and 37,7 g of trans-1-(trans-4-cyanocyclohexyl)-4-(trans-4-n-pentylcyclohexyl)-cyclohexa ne (described in German Patent Application P 3,426,035) dissolved in 40 ml of toluene are added subsequently to a solution of 10,1 g diisopropylamine in 70 ml of THF under nitrogen atmosphere at -10.degree.. The mixture is stirred For 20 minutes.

Subsequently 14,2 g of methyljodide is added at -10.degree.. the mixture is stirred for another 20 minutes at room temperature and worked up as customary. r-1-cyano-1-methyl-trans-4/trans-4-(trans-4-n-pentylcyclohexyl)cyclohexy-1 /-cyclohexane is obtained.

The following positive materials are obtained in an analogous manner:

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-c yclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]- cyclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-c yclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-hexylcyclohexyl)-cyclohexyl]-c yclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]- cyclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-octylcyclohexyl)-cyclohexyl]-c yclohexane

r-1-cyano-1-methyl-trans-4-[trans-4-trans-4-nonylcyclohexyl)-cyclohexyl]-cy clohexane

r-1-cyano-1-methyl-trans-4-[trans-4-(trans-4-decylcyclohexyl)-cyclohexyl]-c yclohexane

The following negative materials are obtained in an analogous manner by alkylation with appropriate alkyl halides:

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-hexylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-ethyl-cis-4-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-propyl-cis-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cycloh exane

r-1-cyano-1-propyl-cis-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-propyl-cis-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cyclo hexane

4-1-cyano-1-propyl-cis-[trans-4-(trans-4-pentylcyclohexyl)cyclohexyl]-cyclo hexane

4-1-cyano-1-propyl-cis-[trans-4-(trans-4-hexylcyclohexyl)cyclohexyl]-cycloh exane

4-1-cyano-1-propyl-cis-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trand-4-pentylcyclohexyl)-cyclohexyl]cycl ohexane

r-1-cyano-1-butyl-cis-4-[trans-4-(trans-4-hexylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-butyl-cis-4-]trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-pentyl-cis-[trans-4-(trans-(methylcyclohexyl)cyclohexyl]-cycloh exane

r-1-cyano-1-pentyl-cis-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-pentyl-cis-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]-cycloh exane

4-1-cyano-1-pentyl-cis-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cycl ohexane

4-1-cyano-1-pentyl-cis-[trans-4-(trans-4-hexylcyclohexyl)cyclohexyl]-cycloh exane

4-1-cyano-1-pentyl-cis-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-ethylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-butylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cyc lohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-hexylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-hexyl-cis-4-[trans-4-(trans-4-heptylcyclo-hexyl)-cyclohexyl]-cy clohexane

r-1-cyano-1-heptyl-cis-[trans-4-(trans-4-ethylcyclohexyl)cyclohexyl]-cycloh exane

r-1-cyano-1-heptyl-cis-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-cycl ohexane

r-1-cyano-1-heptyl-cis-[trans-4-(trans-4-butylcyclohexyl)cyclohexyl]cyclohe xane

4-1-cyano-1-heptyl-cis-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-cycl ohexane

4-1-cyano-1-heptyl-cis-[trans-4-(trans-4-hexylcyclohexyl)cyclohexyl]-cycloh exane

4-1-cyano-1-heptyl-cis-[trans-4-(trans-4-heptylcyclohexyl)-cyclohexyl]-cycl ohexane.

Example 25

A mixture of 12.4 g of 4-(trans-4-n-propylcyclohexyl)-1-methyl-3-cyclohexene-1-carbonitrile [obtainable by reaction of trans-4-propylcyclohexanecarboxylic acid chloride with vinyltrimethylsilane under AlCl.sub.3 catalysis according to J. P. Pillot, J. Dunogues and R. Calas, Bull. Soc. Chem. Fr. 2143 (1975); C.r. hebd. Seanc. Acad. Sci., Paris 278, 787, 789 (1974), reaction of the resulting trans-4-n-propylcyclohexyl vinyl ketone with the Tebbe reagent or with methylenetriphenylphosphorane by the Wittig method to give 2-(trans-4-n-propylcyclohexyl)-1,3-butadiene, and reaction of the diene with methyl methacrylate according to W. Kreiser, P. Below and L. Ernst, Liebigs Ann. Chem. 1985, 194; G. Bartels, thesis, Technical University of Braunschweig, 1978, to give methyl 4-(4-trans-n-propylcyclohexyl)-1-methyl-3-cyclohexene-1-carboxylate by a regiospecific route, and basic hydrolysis of the latter compound followed by conversion to the nitrile by the customary route, via the acid chloride and amide], 40 g of Raney nickel and 200 ml of ethanol is hydrogenated at room temperature. After the customary working-up, r- 1-cyano-1-methyl-trans-4-(trans-4-n-propylcyclohexyl)-cyclohexane is obtained.

The following compounds are prepared in an analogous manner:

r-1-cyano-1-methyl-4-trans-4-(trans-4-ethylcyclohexyl)cyclohexane

r-1-cyano-1-methyl-trans-4-(trans-4-butylcyclohexyl)cyclohexane

r-1-cyano-1-methyl-trans-4-(trans-4-pentylcyclohexyl)cyclohexane

r-1-cyano-1-methyl-trans-4-(trans-4-hexylcyclohexyl)cyclohexane

r-1-cyano-methyl-trans-4-(trans-4-heptylcyclohexyl)cyclohexane.

Example 26

A solution of 26.6 g of r-1-methyl-1-n-pentyl-cis-4-(trans-4-hydroxycyclohexyl)-cyclohexane [obtainable analogously to Example 22 by hydrogenation of the corresponding phenol] in 250 ml of tetrahydrofuran is added dropwise, at 50.degree. C., to a stirred mixture of 22 g of n-butyl iodide and 8.9 g of KH in 250 ml of tetrahydrofuran, and stirring is continued for a further 2 hours at 50.degree. C. After the customary working-up, r-1-methyl-1-n-pentyl-cis-4-(trans-4-butoxycyclohexyl)-cyclohexane is obtained.

The following compounds are prepared in an analogous manner:

r-1-methyl-1-pentyl-cis-4-(trans-4-ethoxycyclohexyl)cyclohexane

r-1-methyl-1-pentyl-cis-4-(trans-4-propoxycyclohexyl)cyclohexane

r-1-methyl-1-pentyl-cis-4-(trans-4-pentoxycyclohexyl)cyclohexane

r-1-methyl-1-pentyl-cis-4-(trans-4-propionyloxycyclohexyl)-cyclohexane

r-1-methyl-1-pentyl-cis-4-(trans-4-butyryloxycyclohexyl)cyclohexane

r-1-methyl-1-propyl-cis-4-(trans-4-ethoxycyclohexyl)cyclohexane

r-1-methyl-1-propyl-cis-4-(trans-4-propoxycyclohexyl)cyclohexane

r-1-methyl-1-propyl-cis-4-(trans-4-pentoxycyclohexyl)cyclohexane

r-1-methyl-1-propyl-cis-4-(trans-4-propionyloxycyclohexyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(trans-4-butyryloxycyclohexyl)cyclohexane.

The following compounds are obtained from r-1-methyl-1-n-pentyl-cis-4-hydroxyphenyl-cyclohexane [obtainable analogously to Example 22 by ether cleavage of the corresponding anisole] by etherification with an appropriate alkyl halide in the presence of potassium carbonate:

r-1-methyl-1-pentyl-cis-4-ethoxyphenyl-cyclohexane

r-1-methyl-1-pentyl-cis-4-propoxyphenyl-cyclohexane

r-1-methyl-1-pentyl-cis-4-butoxyphenyl-cyclohexane

r-1-methyl-1-pentyl-cis-4-pentoxyphenyl-cyclohexane

r-1-methyl-1-pentyl-cis-4-propionyloxyphenyl-cyclohexane

r-1-methyl-1-pentyl-cis-4-butyryloxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-ethoxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-propoxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-butoxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-pentoxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-propionyloxyphenyl-cyclohexane

r-1-methyl-1-propyl-cis-4-butyryloxyphenyl-cyclohexane.

Example 27

A mixture of 10.9 g of 1-methyl-1-n-pentyl-4-(p-(n-propyl)-phenyl)-3-cyclohexene [obtainable from 4-n-pentyl-4-methylcyclohexanone by reaction with a Grignard solution, obtained from p-(n-propyl)-bromobenzene, and elimination of water], 40 g of Raney nickel and 200 ml of ethanol is hydrogenated at room temperature. After the customary working-up, r-1-methyl-1-n-pentyl-cis-4-(p-(n-propyl)-phenyl)-cyclohexane is obtained.

The following compounds are prepared in an analogous manner:

r-1-methyl-1-pentyl-cis-4-(p-ethylphenyl)-cyclohexane

r-1-methyl-1-pentyl-cis-4-(p-butylphenyl)-cyclohexane

r-1-methyl-1-pentyl-cis-4-(p-pentylphenyl)-cyclohexane

r-1-methyl-1-pentyl-cis-4-(p-heptylphenyl)-cyclohexane

r-1-methyl-1-butyl-cis-4-(p-ethylphenyl)-cyclohexane

r-1-methyl-1-butyl-cis-4-(p-propylphenyl)-cyclohexane

r-1-methyl-1-butyl-cis-4-(p-butylphenyl)-cyclohexane

r-1-methyl-1-butyl-cis-4-(p-pentylphenyl)-cyclohexane

r-1-methyl-1-butyl-cis-4-(p-heptylphenyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(p-ethylphenyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(p-propylphenyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(p-butylphenyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(p-pentylphenyl)-cyclohexane

r-1-methyl-1-propyl-cis-4-(p-heptylphenyl)-cyclohexane.

Example 28

2.9 g of 2-/4-(trans-4-n-pentylcyclohexyl)-1-cyanocyclohex-1-yl/-acetaldehyde /obtained by reaction of trans-1-(trans-4-cyanocyclohexyl)-4-n-pentylcyclohexane (described in German Patent 2,702,598) with ethylenoxide followed by conversion of the alcohol to the corresponding aldehyde by reaction with pyridimium chlorochromate/and 20 ml of ether are added to a mixture of 5.4 g of n-butyl-triphenylphosphoniumbromide in 100 ml/of ether and 7,4 ml of n-butyllithium in hexane (1,7M) at -40.degree.. The mixture is stirred at -40.degree. for 2 hours and warmed up. After the customary working-up and isomerisation, r-1-cyano-1-(trans-2-hexenyl)-cis-4-(trans-4-n-pentylcyclohexyl)-cyclohexa ne is obtained.

The following compounds are prepared in an analogous manner (the homologous aldehydes are prepared from the anion of trans-1-(trans-4-cyanocyclohexyl)-4-alkylcyclohexanes by reaction with formic acid ethyl ester, ethylen oxide or oxetane and subsequent reaction with pyridiniumchlorochromate, if necessary. The trans-alkenyl isomers are obtained by conventional isomerisation procedures):

r-1-cyano-1-(trans-2-butenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-2-pentenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-2-heptenyl)-cis-4-(trans-4pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-propenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-butenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-pentenyl)-cis-4-(trans-4-propylcvyclohexyl)-cyclohexan e

r-1-cyano-1-(trans-1-hexenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-heptenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-propenyl)-cis-4-(trans-4-bulylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-butenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-pentenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-hexenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-heptenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-propenyl)-cis-4-(trans-4-pentycyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-butenyl)-cis-4-(trans-4-penlylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-pentenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-hexenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-heptenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-propenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-butenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-pentenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-1-hexenyl)-cis-4-(trans-4-heplylcyclohexyl)-cyclohexane

r-1-cyano-1- (trans-1-heptenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-butenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-pentenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-hexenyI)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-heptenyl)-cis-4-(trans-4-propylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-butenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-pentenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-hexenyl)-cis-4-(trans-4-bulylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-heptenyl)-cis-4-(trans-4-butylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-)-butenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-pentenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-hexenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-heptenyl)-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-butenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-pentenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-hexenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

r-1-cyano-1-(trans-3-heptenyl)-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane

The following examples relate to liquid crystal phases according to the invention.

Example A

A liquid crystal phase is prepared from:

15% of 2-p-cyanophenyl-5-propyl-1,3-dioxane,

23% of 2-p-cyanophenyl-5-butyl-1,3-dioxane,

17% of 2-p-cyanophenyl-5-pentyl-1,3-dioxane,

7% of 4-(4-cyano-4-propylcyclohexyl)-4'-pentylbiphenyl,

12% of 4-cyano-4-heptyl-4'-(trans-4-pentyl-cyclohexylcarbonyloxy)-bicyclohexane,

11% of methyl 4-propyl-4'-heptyl-bicyclohexyl-4'-carboxylate,

6% of p-cyanophenyl p-trans-4-ethylcyclohexyl-benzoate,

7% of p-cyanophenyl p-trans-4-pentylcyclohexyl-benzoate and

2% of p-cyanophenyl p-(o-propylbenzoyloxy)-benzoate.

Example B

A liquid crystal phase is prepared from:

17% of 2-p-cyanophenyl-5-propyl-1,3-dioxane,

25% of 2-p-cyanophenyl-5-butyl-1,3-dioxane,

19% of 2-p-cyanophenyl-5-pentyl-1,3-dioxane,

13% of 2-p-cyanophenyl-5-heptyl-1,3-dioxane,

0.5% of 4-(4-formyl-4-prooylcyclohexyl)-4'-pentylbiphenyl,

0.5% o-trans-4-pentylcyclohexyl-benzonitrile,

14% of 4-cyano-4'-(trans-4-pentylcyclohexyl)-biphenyl,

7% of p-ethoxyphenyl trans-4-propylcyclohexanecarboxylate and

4% of trans-4-propylcyclohexyl trans-4-pentylcyclohexanecarboxylate.

Example C

A liquid crystal phase is prepared from:

9% of trans-4-propylcyclohexyl trans-4-propylcyclohexanecarboxylate,

7% of trans-4-propylcyclohexyl trans-4-pentylcyclohexanecarboxylate,

17% of 2-p-cyanophenyl-5-propyl-1,3-dioxane,

25% of 2-p-cyanophenyl-5-butyl-1,3-dioxane,

18% of 2-p-cyanophenyl-5-pentyl-1,3-dioxane,

7% of 1-fluoro-1-[4'-(trans-4-pentylcyclohexyl)-biphenyl-4-yl]-4-propylcyclohexa ne,

3% of 1-fluoro-1-[4'-(trans-4-propylcyclohexyl)-biphenyl-4-yl]-4-propylcyclohexa ne,

5% of 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propylcyclohexyl)-biphenyl and

9% of p-pentylphenyl p-methoxybenzoate.

Example D

A liquid crystal phase of

10% of 4-pentyl-4'-heptyl-4'-ethylthiobicyclohexane,

17% of 4-pentyl-4'-heptyl-4'-ethylsulfonylbicyclohexane,

9% of 4-propyl-4'-methyl-4'-hexylsulofinylbicyclohexane,

27% of 4-propyl-4'-methyl-4'-heptylsulfinylbicyclohexane,

32% of 4-pentyl-4'-methyl-4'-pentylsulfonylbicyclohexane and

5% of 4-p-cyanophenyl-4'-pentyl-biphenyl

has an excellent dissolving power for pleochroic dyestuffs and is suitable as a base mixture for positive guest/host systems.

Example E

A liquid crystal phase of

20% r-1-cyano-cis-4-(trans-4-butylcyclohexyl)-1-heptylcyclohexane,

21% r-1-cyano-cis-4-(trans-4-pentylcyclohexyl)-1-pentylcyclohexane,

11% trans,trans-4-propyl-4,-methoxycyclohexylcyclohexane,

10% trans,trans-4-propyl-4,-ethoxycyclohexylcyclohexane,

4% trans,trans-4-butylcyclohexyl-cyclohexane-4'-carboxylic acid-trans-4-propylcyclohexylester,

4% trans,trans-4-butylcyclohexyl-cyclohexane-4'-carboxylic acid-trans-4-pentylcyclohexylester,

4% trans,trans-4-propylcyclohexyl-cyclohexane-4'-carboxylic acid-trans-4-propylcyclohexylester,

4% trans,trans-4-propylcyclohexyl-cyclohexane-4'-carboxylic acid-trans-4-pentylcyclohexylester and

22% r-1-cyano-1-(trans-4-pentylcyclohexyl)-cis-4-(trans-4-pentylcyclohexyl)-cy clohexane

has a clear point of 100.degree. and an optical anisotropy of 0.04.

Example F

A liquid-crystalline phase is prepared from

15% of 2-p-cyanophenyl-5-propyl-1,3-dioxane,

23% of 2-p-cyanophenyl-5-butyl-1,3-dioxane,

17% of 2-p-cyanophenyl-5-pentyl-1,3-dioxane,

7% of p-[trans-4-(trans-4-pentyl-4-methylcyclohexyl)-cyclohexyl]-benzonitrile,

12% of 4-cyano-4'-(trans-4-pentylcyclohexyl)-biphenyl,

11% of r-1-cyano-1-methyl-trans-4-(trans-4-propylcyclohexyl)-cyclohexane,

6% of p-cyanophenyl p-trans-4-ethylcyclohexylbenzoate,

7% of p-cyanophenyl p-trans-4-pentylcyclohexylbenzoate and

2% of p-cyanophenyl p-(p-propylbenzoyloxy)-benzoate.

The preceding examples can be repeated with similar success by substituting the generically or specifically described reactants and/or operating conditions of this invention for those used in the preceding examples.

From the foregoing description, one skilled in the art can easily ascertain the essential characteristics of this invention, and without departing from the spirit and scope thereof, can make various changes and modifications of the invention to adapt it to various usages and conditions.

Claims

What is claimed is:

1. A cyclohexane derivative of the formula wherein R.sup.1 and R.sup.2 independently are (a) C.sub.1-15 -alkyl, (b) C.sub.1-15 -alkyl substituted by halo or CN, (c) C.sub.1-15 -alkyl wherein one or two non-adjacent CH.sub.2 groups are replaced by at least one of --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--, --S--, the maximum number of C-atoms still being 15, (d) F, (e) Cl, (f) Br, (g) CN or (h) R.sup.3 --(A.sup.3).sub.p --Z.sup.2 --, A.sup.1 is --A--, --A.sup.4 --Z.sup.3 --A--or --A--Z.sup.3 --A.sup.4 --, A is 1,4-cyclohexylene which is additionally substituted in the 1- or 4-position by CN, A.sup.2, A.sup.3 in each case independently are (a) 1,4-and A.sup.4 phenylene, (b) 1,4-phenylene substituted by one or two F, Cl, CH.sub.3 or CN, (c) any of groups (a) or (b) wherein one or two CH groups are replaced by N atoms, (d) 1,4-cyclohexylene, (e) 1,4-cyclohexylene wherein one or two non-adjacent CH.sub.2 groups are replaced by O-atoms, (f) 1,4-cyclohex-1-enyl, Z.sup.1, Z.sup.2 each independently are --CO--O--, --O--CO--, and Z.sup.3 --OCH.sub.2 --, --CH.sub.2 O--, --CH.sub.2 CH.sub.2 --or a single bond, R.sup.3 is (a) C.sub.1-15 -alkyl, (b) C.sub.1-15 -alkyl, substituted by halo or CN, (c) a group (a)-(b) wherein one or two non-adjacent CH.sub.2 groups are replaced by one of --O--, --CO--, --O--CO--, --CO--O--, --C.tbd.C--, --CH.dbd.CH--or --S--, the maximum number of C-atoms still being 15, (d) F, (e) CI, (f) Br or (g) CN and is 1 or 2, and when p=2, the groups A.sup.3 can be identical or different.

2. A compound of claim 1 of the formula or

3. A compound of claim 1 of the formula

4. A compound of claim 1 of the formula --R.sup.3 --R.sup.2 --R.sup.2 --R.sup.3 or --R.sup.3

5. A phase of claim 1 of the formula --R.sup.3 --R.sup.3 --R.sup.3 --R.sup.3 --R.sup.3 --R.sup.3 --A.sup.3 --R.sup.3 --A.sup.3 --R.sup.3 --A.sup.3 --R.sup.3 --A.sup.3 --R.sup.3 --A.sup.3 --R.sub.3 or --A.sup.3 --R.sup.3

6. A phase of claim 1 of the formula wherein the Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl and Pyr is pyrimidine-2,5-diyl.

7. A compound of claim 1 of the formula --R.sup.2 wherein R.sup.1 and R.sup.2 are each independently, C.sub.1-10 straight chain alkyl or C.sub.1-10 branched alkyl of only one chain branching, in each of which one or two CH.sub.2 groups is optionally replaced by 0 atoms; or --O--COR; A.sup.1 and A.sup.2 are each independently 1,4-phenylene, which is unsubstituted or substituted by 1-4 F atoms; or 1,4-cyclohexylene; A is 1,4-cyclohexylene which is additionally substituted in the 1-position or in the 4-position by CN; Z.sup.1 and Z.sup.2 are each independently --CO--O--, --O--CO--, --CH.sub.2 CH.sub.2 --, --OCH.sub.2 --, --CH.sub.2 O-- or a single bond; R is alkyl of 1-5 C atoms; m is 1 or 2 and n is 0 or 1, wherein when m is 2, the two A.sup.1 groups are identical or different from one another.

8. A compound of claim 7 of the formula

9. A compound of claim 7 of the formula

10. A compound of claim 7 of the formula

11. A compound of claim 7 of the formula

12. A compound of claim 7 of the formula wherein Phe is 1,4-phenylene, and Cy is 1,4-cyclohexylene.

13. A compound of claim 7 of the formula wherein Phe is 1,4-phenylene, and Cy is 1,4-cyclohexylene.

14. A compound of claim 7 of the formula wherein Phe is 1,4-phenylene, and Cy is 1,4-cyclohexylene.

15. A compound of claim 7 wherein R.sup.1 and R.sup.2, independently, are each alkyl or oxa-containing alkyl.

16. A compound of claim 7 wherein A.sup.1 and A.sup.2, independently, are each 1,4-cyclohexylene or 1,4-phenylene.

17. A compound of claim 7 wherein Z.sup.1 and Z.sup.2 are each single bonds.

18. A compound of claim 7 wherein m is 1 and n is 0.

19. A compound of claim 7 of the formula wherein Phe is 1,4-phenylene, and Cy is 1,4-cyclohexylene.

20. A compound of claim 7 wherein the groups R.sup.1 --(A.sup.1).sub.m --Z.sup.1 -- and --Z.sup.2 --(A.sup.2).sub.n --R.sup.2 are in the trans-position in relation to one another, and the 1-substitutent on A is in the cis-position in relation to the group opposite to it.

21. r-1-cyano-1-pentyl-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane, a compound of claim 7.

22. A compound of claim 7 of the formula ##STR6## wherein R.sup.1 is alkyl of 2-7 C atoms, R.sup.2 is alkyl of 2-10 C atoms, or alkyl of 2-10 C atoms wherein one CH.sub.2 group is replaced by an oxygen atom and Cy is 1,4-cyclohexylene.

23. A compound of claim 22 which is (a) r-1-cyano-1-ethyl-cis-4-(trans-4-ethylcyclohexyl)-cyclohexane, (b) r-1-cyano-1-ethyl-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane, (c) r-1-cyano-1-propyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (d) r-1-cyano-1-propyl-cis-4-(trans-4-butylcyclohexyl)-cyclohexane, (e) r-1-cyano-1-propyl-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane, (f) r-1-cyano-1-propyl-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane, (g) r-1-cyano-1-isopropyl-cis-4-(trans-4-heptyl-cyclohexyl)cyclohexane, (h) r-1-cyano-1-butyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (i) r-1-cyano-1-butyl-cis-4-(trans-4-butylcyclohexyl)-cyclohexane, (j) r-1-cyano-1-pentyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (k) r-1-cyano-1-pentyl-cis-4-(trans-4-butylcyclohexyl)-cyclohexane, (l) r-1-cyano-1-pentyl-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane, (m) r-1-cyano-1-pentyl-cis-4-(trans-4-heptylcyclohexyl)-cyclohexane, (n) r-1-cyano-1-hexyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (o) r-1-cyano-1-hexyl-cis-4-(trans-4-butylcyclohexyl)-cyclohexane, (p) r-1-cyano-1-heptyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (q) r-1-cyano-1-heptyl-cis-4-(trans-4-butylcyclohexyl)-cyclohexane, (r) r-1-cyano-1-heptyl-cis-4-(trans-4-pentylcyclohexyl)-cyclohexane, (s) r-1-cyano-1-octyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (t) r-1-cyano-1-nonyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (u) r-1-cyano-1-decyl-cis-4-(trans-4-propylcyclohexyl)-cyclohexane, (v) r-1-cyano-1-ethoxymethyl-cis-4-(trans-4-pentylcyclohexyl)cyclohexane.

24. A compound of claim 7 of the formula ##STR7## wherein R.sup.1 is alkyl of 2-7 C atoms, A.sup.2 is 1,4-cyclohexylene or 1,4-phenylene and R.sup.2 is alkyl of 2-10 C atoms.

25. A compound of claim 24 which is (a) trans-4-propylcyclohexyl 1-cyano-trans-4-pentyl-cyclohexane-r-1-carboxylate, (b) trans-4-butylcyclohexyl 1-cyano-trans-4-pentyl-cyclohexane-r-1-carboxylate, (c) trans-4-pentylcyclohexyl 1-cyano-trans-4-pentyl-cyclohexane-r-1-carboxylate, (d) trans-4-hexylcyclohexyl 1-cyano-trans-4-pentyl-cyclohexane-r-1-carboxylate, or (e) p-propylphenyl 1-cyano-trans-4-pentyl-cyclohexane-r-1-carboxylate.

26. A compound, of claim 1 of the formula --R.sup.2' wherein R.sup.1' and R.sup.2' are each C.sub.1-10 -alkyl; C.sub.1-10 -alkyl wherein one or two non-adjacent CH.sub.2 groups are replaced by 0 atoms or --CH.dbd.CH--, the maximum number of C-atoms still being 15; F; Cl,; Br; CN; --COOR; --O--COR; or --C.tbd.C--R.sup.340 , A.sup.1' and A.sup.2' are each 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, 1,4-phenylene, pyridazine-3,6-diyl or pyrimidine-2,5-diyl, or one of the last three groups C-substituted by one or two of F, Cl, CH.sub.3, or CN, A is 1,4-cyclohexylene substituted in the 1- or 4-position by CN, Z.sup.0 and Z.sup.1' are each --CO--O--, --O--CO--, --CH.sub.2 --CH.sub.2 --, --OCH.sub.2, --CH.sub.2 --O--or a single bond, R.sup.3' is alkyl of 1-7 C atoms, R is alkyl of 1-10 C atoms and m and n are each independently 1 or 2, and wherein (m+n).gtoreq.3or, when Z.sup.0 is a single bond and Z.sup.1' is not a single bond, .gtoreq.2 and when m=2 or n=2, all groups A.sup.1' , A.sup.2' and Z.sup.1' which are present are identical or different.

27. A compound of claim 26 of the formula

28. A compound, of claim 26 of the formula wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Pyn is pyridazine-3,6-diyl and Pyr is pyrimidine-2,5-diyl.

29. A compound of claim 1 of the formula wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene, Dio is 1,3-dioxane-2,5-diyl, Pyn is pyridazine-3,6-diyl and Pyr is pyrimidine-2,5-diyl.

30. A phase of claim 26 wherein said cyclohexane derivative is of the formula wherein Phe is 1,4-phenylene, Cy is 1,4-cyclohexylene and Dio is 1,3-dioxane-2,5-diyl.

31. A compound of claim 26 of the formula ##STR8##

32. A compound of claim 26 of the formula ##STR9##

33. A compound of claim 1, wherein A is ##STR10## wherein the substituents in the 1- and 4-positions are in the trans-position relative to one another, while the CN group is in the position cis to the opposite group.

Patent Citations (5)

Patent	Date	Inventor
US4181625	1980-01-01	Eidenschink et al.
US4510069	1985-04-01	Eidenschink et al.
US4629581	1986-12-01	Petrzilka et al.
US4659499	1957-04-01	Ferrato
DEX3328638	1985-02-01

Abstract

Description