DE3231707A1 - Cyclohexane derivatives - Google Patents

Abstract

Novel cyclohexane derivatives of the formula I R<1>-(A<1>)m-Z<1>-A-Z<2>-(A<2>)n-R<2> (I> in which R<1> and R<2> denote in each case H, an alkyl group having 1-10 C atoms which can also be interrupted by one or two O atoms, or R<1> and R<2> are F, Cl, Br or CN, A<1> and A<2> in each case denote 1,4-phenylene, 1,4-cyclohexylene, 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo(2,2,2)octylene or pyrimidine-2,5-diyl groups, unsubstituted or substituted by 1-4 F atoms, A denotes a 1,4-cyclohexylene group which is substituted in the 1- and/or 4-position by F, Cl, Br and/or CN and to which one or two further F, Cl or Br atoms and/or CN groups can be attached, Z<1> and Z<2> denote in each case -CO-O-, -O-CO-, -CH2CH2-, -OCH2-, -CH2O- or a single bond, m denotes 1 or 2 and n denotes 0 or 1, where in the case of m = 2 the two groups A<1> can be identical or different from each other, and the acid addition salts of the basic compounds amongst these are suitable for use as components in liquid-crystalline dielectrics.

Description

Cyclohexane derivatives

The invention relates to new cyclohexane derivatives of the formula I R¹- (A¹) m-Z¹-A-Z²- (A²) n-R² I wherein R¹ and R² are each H, an alkyl group with 1 - 10 carbon atoms, which is also through one or two O atoms can be interrupted, F, Cl, Br or CN, A1 and A2 respectively 1,4-phenylene, 1,4-cyclohexylene, unsubstituted or substituted by 1 - 4 carbon atoms 1,3-dioxane-2,5-diyl, piperidine-1,4-diyl, 1,4-bicyclo (2,2,2) -octylene, or pyrimidine-2,5-diyl groups, A is a 1,4-cyclohexylene group substituted in the 1- and / or 4-position by F, Cl, Br and / or CN, which can carry 1 or 2 further F, Cl or Br atoms and / or CN groups, Z1 and z2 in each case -CO-O-, -O-CO-, -CH2CH2-, -OCH2-, -CH2O- or a single bond, m is 1 or 2 and n is 0 or 1, with the two groups A1 being the same for m = 2 or can be different from one another, as well as the acid addition salts of the basic under these connections.

For the sake of simplicity, in the following "Phe" means a 1,4-phenylene group, "Cy" a 1,4-cyclohexylene group, "Dio" a 1,3-dioxane-2,5-diyl group, "Bi" a Bicyclo- (2,2,2) -octylene group, "Pip" a piperidine-1,4-diyl group, and "Pyr" a Pyrimidine-2,5-diyl group, these groups, in particular the 1,4-phenylene group, unsubstituted or substituted by 1 to 4 fluorine atoms.

Similar compounds are known from EP-OS 19 665, for example. the However, in contrast to the present compounds, they contain compounds specified there no 1,1,4-trisubstituted cyclohexane rings.

The compounds of the formula I can be used as similar compounds as Components of liquid crystalline dielectrics are used, in particular for displays, based on the principle of the twisted cell, the guest-host effect, the effect of Deformation of erect phases or the effect of dynamic scattering are based.

The invention was based on the object of providing new stable liquid-crystalline or to find mesogenic compounds that are liquid-crystalline components Dielectrics are suitable. That job was done by providing the connections of formula I solved.

It has been found that the compounds of formula I as components liquid-crystalline dielectrics are eminently suitable. In particular, are with their help stable liquid crystalline phases with strongly negative dielectric Anisotropy and thus a small threshold or control voltage of electro-optical effects, very small optical anisotropy and comparatively low viscosity can be produced.

With the provision of the compounds of the formula I is also in general the range of liquid-crystalline substances, which are classified under different application-related aspects for the production of nematic mixtures, widened considerably.

The compounds of the formula I have a wide range of applications. Depending on the choice of substituents, these compounds can be used as Base materials are used from which liquid-crystalline dielectrics are predominantly used Part are composed; however, compounds of the formula I can also be liquid-crystalline Base materials from other classes of compounds are added, for example the dielectric and / or optical anisotropy of such a dielectric reduce. The compounds of formula I are also suitable as intermediates for Manufacture of other substances that are components of liquid crystalline dielectrics let use.

The compounds of the formula I are colorless in the pure state and form liquid crystalline mesophases in one favorable for electro-optical use located temperature range. They are very stable chemically, thermally and against light.

The invention thus relates to the compounds of the formula I and a process for their preparation, characterized in that a compound which otherwise corresponds to formula I, but instead of one or more H atoms Contains reducible groups and / or C-C bonds, with a reducing agent treated, or that one of a compound which otherwise corresponds to formula I, but instead of the radical A contains an 1-cyclohexene-1,4-diyl group, 1 or 2 more F, Cl or Br atoms and / or CN groups can carry a compound of the formula HX (where X is F, Cl, Br or CN) is added, or that one for the preparation of Esters of the formula I (in which z1 and / or z2 are —CO — O— or —O — CO—) have a corresponding Carboxylic acid or one of its reactive derivatives with a corresponding one Reacts alcohol or one of its reactive derivatives, or that one for the production of dioxane derivatives of the formula I (in which A1 and / or A2 are 1,3-dioxane-2,5-diyl) reacts a corresponding aldehyde with a corresponding diol, or that for the preparation of nitriles of the formula I (in which R1 and / or R2 are CN and / or in which A is substituted by at least one CN group) a corresponding one Carboxamide dehydrated or a corresponding carboxylic acid halide with Reacts sulfamide, or that for the preparation of nitriles of the formula I (in which A denotes a 1,4-cyclohexylene group substituted in the 1-position by CN) Acetonitrile of the formula II R1- (Al) m-Zl-CH2CN II in which R¹, A11, Z1 and m have the meanings given have, with a compound of the formula III (X1-CH2-CH2) 2CH-Z2- (A2) n-R2 III wherein X1 means Cl, Br, J, OH or a reactive esterified OH group and R2, A2, z2 and n have the meanings given, or that one for the production of nitriles of the formula I (in which A is substituted in the 1- or 4-position by CN 1,4-Cyclohexylene group means which are additionally represented by one or two F atoms and / or CN groups can be substituted; in which further. the one of the leftovers Z1 or z2 denotes a single bond) a nitrile of the formula IV Q1-A3CN IV in which Q1 (a) R¹- (A¹) m-Z¹- or (b) R²- (A²) n-Z²- and A3 is an unsubstituted or a 1,4-cyclohexylene group which is mono- or disubstituted by F and / or CN and R¹, R², A¹, A², Z¹, Z², m and n have the meanings given with one A compound of the formula V Q²-X¹ V wherein Q² is (a) R¹²- (A¹²) n- or (b) R¹- (A¹) m and X¹, R1, R², All A2, m and n have the meanings given, converts, or that for the preparation of ethers of the formula 1 (in which R1 and / or R2 one by one or two O atoms denote interrupted alkyl chain and / or Z1 and / or z2 a -OCH2- or -CH2O- group) etherifies a corresponding hydroxy compound, and or that optionally a chlorine or bromine compound of the formula I (in which R1 and / or R2 is Cl or Br and / or in which A is replaced by at least one chlorine or bromine atom is substituted) with a cyanide, and / or that optionally one Base of formula 1 by treatment with an acid in one of its acid addition salts converts, or that you optionally a compound of formula I from one of its Acid addition salts liberated by treatment with a base.

The invention also relates to the use of the compounds of the formula I as components of liquid-crystalline dielectrics. Subject of the invention are also liquid-crystalline dielectrics with a content of at least one Compound of the formula I and electro-optical display elements, the dielectrics of this type contain.

Above and below have R1, R2, Al, A2 A, Z1, z2 m, n, X1, Q1, Q2 and A3 have the meaning given, unless expressly stated otherwise is.

The compounds of the formula I accordingly include compounds of the sub-formulas Ia (with two rings), Ib and Ic (each with three rings) and Id (with four rings): R¹-A¹-Z¹-A-Z²-R² Ia R¹-A¹-Z¹-A-Z²-A²-R² Ib R¹- (A¹) 2-Z¹-A-Z²-R² Ic R¹- (A¹) 2-Z¹-A-Z²-A²-R² Id.

The preferred compounds of the partial formula Ia include those of the Part formulas Ie to Ij: R¹-Phe-Z¹-A-Z²-R² Ie R¹-Cy-Z¹-A-Z²-R² If R¹-Dio-Z¹-A-Z²-R² Ig R¹-Pip-Z¹-A-Z²-R² Ih R¹-Bic-Z¹-A-Z²-R² Ii R¹-Pyr-Z¹-A-Z²-R² Ij are among them those of the formulas Ie, If and Ig are particularly preferred.

Of the compounds of the sub-formulas Ib, Ic and Id are those of the sub-formulas Ik to Iz are particularly preferred: R¹-Phe-Z¹-A-Z²-Phe-R² Ik R¹-Dio-Z¹-A-Z²-Cy-R² II R¹-Cy-Z¹-A-Z²-Phe-R² Im R¹-Cy-Z¹-A-Z²-Cy-R² In R¹-Phe-Phe-Z¹-A-Z²-R² Io R¹-Phe-Cy-Z¹ -A-Z²-R² Ip R¹-Cy-Phe-Z¹-A-Z²-R² Iq R¹-Cy-Cy-Z¹-A-Z²-R² Ir R¹-Phe-Phe-Z¹-A-Z²-Phe-R² Is R¹-Phe-Phe -Z¹-A-Z²-Cy-R² It R¹-Phe-Cy-Z¹-A-Z²-Phe-R² Iu R¹-Phe-Cy-Z¹-A-Z²-Cy-R² Iv R¹-Cy-Phe-Z¹-A-Z²-Phe-R² Iw R¹-Cy-Phe-Z¹-A-Z²-Cy-R² Ix R¹-Cy-Cy-Z¹-A-Z²-Phe-R² Iy R¹-Cy-Cy-Z¹-A-Z²-Cy-R² Iz In the compounds of the formulas above and below, mean R1 and R2 are preferably alkyl, furthermore alkoxy (especially if these radicals are on a Phe group) or another oxaalkyl group.

A1 and A2 are preferably Cy or Phe, furthermore preferably Dio or Pip; the compound of the formula I preferably contains no more than one of the radicals Dio, Pip, Bic or Pyr.

A is preferably a l-X-1,4-cyclohexylene group, which has no other Bears substituents and in which X is preferably CN, furthermore F, C1 or Br.

7 and z2 are preferably single bonds, secondly preferred -CO-O- or -0-CO groups.

m is preferably 1, n is preferably 0.

X1 is preferably C1 or Br, but also J, OH or reactive esterified OH such as alkylsulfonyloxy with in particular 1 - 6 carbon atoms (e.g. methylsulfonyloxy) or arylsulfonyloxy with in particular 6-10 carbon atoms (e.g. phenyl, p-tolyl or Naphthylsulfonyloxy).

In the compounds of the formulas above and below, the Alkyl radicals, which are also of one ("alkoxy" or "oxaalkyl") or two O atoms ("alkoxyalkoxy" or "dioxaalkyl") can be interrupted, straight-chain or branched. Preferably if they are straight-chain, they have 2, 3, 4, 5, 6 or 7 carbon atoms and are therefore preferred Ethyl, propyl, butyl, pentyl, hexyl, heptyl, ethoxy, propoxy, butoxy, pentoxy, hexoxy, Heptoxy, 2-oxapropyl (= methoxymethyl), 2- (= ethoxymethyl) or 3-oxabutyl (= 2-methoxyethyl), 2-, 3- or 4-oxapentyl, 2-, 3-, 4- or 5-oxahexyl, 2-, 3-, 4-, 5- or 6-oxaheptyl, also methyl, octyl, nonyl, decyl, methoxy, octoxy, nonoxy, Decoxy, 2-, 3-, 4-, 5-, 6- or 7-oxaoctyl, 2-, 3-, 4-, 5-, 6-, 7- or 8-oxanonyl, 2-, 3-, 4-, 5-, 6-, 7-, 8- or 9-oxadecyl, 1,3-dioxabutyl (= methoxymethoxy), 1,3-, 1,4- or 2,4-dioxapentyl, 1,3-, 1,4-, 1,5-, 2,4-, 2,5- or 3,5-dioxahexyl, 1,3-, 1,4-, 1,5-, 1,6-, 2,4-, 2,5-, 2,6-3,5-, 3,6- or 4,6-dioxaheptyl.

Compounds of the formulas I and Ia to Iap with branched wing groups R1 and R2 can occasionally because of a better solubility in the usual Liquid-crystalline base materials are important, but especially as chiral Dopants if they are optically active. Include branched groups of this type usually no more than one chain branch. Preferred branched radicals R1 and R2 are isopropyl, 2-butyl (= 1-methylpropyl), isobutyl (= 2-methylpropyS), 2-methylbutyl, isopentyl (= 3-methylbutyl), 2-methylpentyl, 3-methylpentyl, 2-ethylhexyl, 2-propylpentyl, 1-sopropoxy, 2-methylpropoxy, 2-methylbutoxy, 3-methylbutoxy, 2-methylpentoxy, 3-methylpentoxy, 2-ethylhexoxy, 1-methylhexoxy, 1-methylheptoxy, 2-oxa-3-methylbutyl, 3-oxa-4-methylpentyl.

Among the compounds of the formulas I and Ia to Iz are those preferred, in which at least one of the radicals contained therein is one of the specified has preferred meanings. Particularly preferred smaller groups of compounds are those of the formulas Iaa to Iat: R²-A¹-Z¹-A-R² Iaa R¹-Phe-Z¹-A-R² Iab R¹-Phe-A-R² Iac R1-Phe-CO-O-A-R2 1 ad R1 -Phe-O-CO-A-R2 Iae R1 -Phe-CH2CH2-A-R2 Iaf R¹-Phe-O-CH2-A-R² Iag R¹-Phe-CH2-O-A-R² Iah R¹-Cy-Z¹-A-R² Iai R1-Cy-A-R2 Iaj R¹-Cy-CO-O-A-R² Iak R¹-Cy-O-CO-A-R² Ial R¹-Cy-CH2CH2-A-R² Iam R¹-Cy-O-CH2-A-R² Ian R¹-Cy-CH2-O-A-R² Iao R¹-Dio-A-R² Iap R¹-Pip-A-R² Iaq R¹-Bic-A-R² Iar R¹-Pyr-A-R² Ias R¹-Phe-Phe-A-R² Iat.

In the compounds of the above-mentioned formulas, the group A contains a substituent X which can be in the 1- or 4-position. For example, the compounds of the formula I include those of the sub-formulas I 'and I "below (whereby the cyclohexane ring can additionally carry 1 or 2 further F, Cl or Br atoms and / or CN groups). In this sense, compounds of the specified formulas I and Ia to Iat are also particularly preferred in which the radical A in each case means.

Those stereoisomers are preferred in which the groups R¹- (A¹) m-Z¹- and -Z2- (A2) n-R2 are in the trans position to one another, while the substituent x is in the cis position to the opposite group.

For example, the following stereoisomers of the compounds of the formula I 'are preferred: Those of the above-mentioned formulas which contain one or more of the groups Dio, Pip and / or Pyr each encompass the two possible 2,5- or 1,4-positional isomers. For example, the partial formula Iap encloses the 2-R1-5- (A-R2) -l, 3-dioxanes and the 2- (A-R2) -5-R1-1,3-dioxanes, the partial formula Iaq the 1 -R1-4- (A-R2) -piperidines and the 1- (A-R²) -4-R¹-piperidines.

The compounds of the formula I are made according to methods known per se as they are in the literature (e.g. in the standard works such as Houben-Weyl, Methods of Organic Chemistry, Georg-Thieme-Verlag, Stuttgart) are described, under reaction conditions that are known and known for the reactions mentioned are suitable. It is also possible to use what is known per se but is not mentioned here in more detail Make use of variants.

If desired, the starting materials can also be formed in situ, so that they are not isolated from the reaction mixture, but immediately further to the compounds of formula I.

Thus, the compounds of the formula I can be prepared by a compound that otherwise corresponds to formula I, but instead of hydrogen atoms contains one or more reducible groups and / or C-C bonds, reduced.

Preferred reducible groups are carbonyl groups, in particular keto groups, also, for example, free or esterified hydroxyl groups or aromatically bound halogen atoms. Preferred starting materials for the reduction correspond of the formula I, but can instead of a cyclohexane ring a cyclohexene ring or Cyclohexanone ring and / or instead of a -CH2CH2- group a -CH = CH- group or contain a -CH2-CO group.

The reduction is expediently carried out by catalytic hydrogenation Temperatures between about 0 ° and about 200 ° and pressures between about 1 and 200 bar. In an inert solvent, e.g. an alcohol such as methanol, ethanol or isopropanol, an ether such as Tetrahydrofuran (THF) or dioxane, an ester such as ethyl acetate, a carboxylic acid such as acetic acid or a hydrocarbon like cyclohexane.

Useful catalysts are noble metals such as Pt or Pd, those in the form of oxides (e.g. PtO2, PdO), on a carrier (e.g. Pd on carbon, calcium carbonate or strontium carbonate) or in finely divided form (e.g. Pt-Mohr) can.

Compounds of the formula I are still available by calling on a corresponding cyclohexene derivative (which corresponds to formula I, but instead of of the radical A contains a l-cyclohexene-1,4-diyl group, the 1 or 2 more F-, May carry Cl or Br atoms and / or CN groups) a compound of the formula EX (Fluorine, chlorine, bromine or hydrogen cyanide) attaches.

This addition works, for example, in the presence of an inert solvent, z. B. a halogenated hydrocarbon such as CH2Cl2 or CHCl3, a nitrile such as acetonitrile or an amide such as dimethylformamide (DMF) at temperatures between about -10 and +150 ° and pressures between about 1 and 100 bar. An addition of catalysts can be beneficial, e.g. ECN addition can be achieved by adding palladium-bis- [2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis (diphenylphosphino) butane] be catalyzed.

Esters of the formula I (T1 and / or Z² = -CO-O- or -O-CO-) can also by esterification of corresponding carboxylic acids of the formulas R1 Rl- (Al) m-COOH, R¹- (A¹) m-Z¹-A-COOH, R2- (A2) n-COOH or R2- (A2) n-Z2-A-COOH (or their reactive derivatives) with Alcohols or phenols of the formulas R²- (A²) n-Z²-A-OH, R²- (A²) n-OH, R¹- (A¹) m -Z¹-A-OH or R¹- (A¹) m-OH (or their reactive derivatives) will.

Suitable reactive derivatives of the carboxylic acids mentioned are in particular the acid halides, especially the chlorides and bromides, and also the Anhydrides, e.g.

also mixed anhydrides of the formulas R¹- (A¹) m-CO-O-COCH3, R¹- (A¹) m-Z¹-A-CO-O-COCH3, R²- (A²) n-CO-O-COCH3 and R²- (A²) n -Z²-A-CO-O-COCH3, azides or esters, in particular Alkyl esters with 1 - 4 carbon atoms in the alkyl group.

As reactive derivatives of the alcohols mentioned or

Phenols come in particular the corresponding metal alcoholates or Phenolates of the formulas R2- (A2) n -Z2-A-OM, R2- (A2) n-OM, R1- (A1) m -Z1 -A-OM and R1- (Al) m-OM contemplated in which M is an equivalent of a metal, preferably an alkali metal like Na or K, means.

The esterification is advantageous in the presence of an inert solvent carried out. Ethers such as diethyl ether, di-n-butyl ether, THF, dioxane or anisole, ketones such as acetone, butanone or cyclohexanone, amides such as DMF or phosphoric acid hexamethyltriamide, hydrocarbons such as benzene, toluene or Xylene, halogenated hydrocarbons such as carbon tetrachloride or tetrachlorethylene and sulfoxides such as dimethyl sulfoxide or sulfolane. Solvents immiscible with water can at the same time be advantageous for azeotropic distillation of the esterification formed water can be used. Occasionally there can also be an excess of one organic base, e.g. pyridine, quinoline or triethylamine as a solvent for the esterification can be applied. The esterification can also take place in the absence of a Solvent, e.g. by multiple heating of the components in the presence of sodium acetate. The reaction temperature is usually between -50 ° and +250 °, preferably between -20 ° and +80 °. With these Temperatures are the esterification reactions usually after 15 minutes to 48 Hours ended.

In detail, the reaction conditions for the esterification largely depend on the nature of the raw materials used. So it becomes a free carboxylic acid with a free alcohol or phenol usually in the presence of a strong acid, for example a mineral acid such as hydrochloric acid or sulfuric acid. One the preferred mode of reaction is the conversion of an acid anhydride or in particular of an acid chloride with an alcohol, preferably in a basic medium, wherein as bases in particular alkali metal hydroxides such as sodium or ralium hydroxide, alkali metal carbonates or hydrogen carbonates such as sodium carbonate, sodium hydrogen carbonate, potassium carbonate or potassium hydrogen carbonate, alkali metal acetate such as sodium or potassium acetate, Alkaline earth metal hydroxides such as calcium hydroxide or organic bases such as triethylamine, Pyridine, lutidine, collidine or quinoline are important. Another preferred one Embodiment of the esterification consists in that the alcohol or

the phenol first into the sodium or potassium alcoholate or phenolate transferred, e.g. by treatment with ethanolic sodium or potassium hydroxide solution, this isolated and mixed with sodium hydrogen carbonate or potassium carbonate with stirring suspended in acetone or diethyl ether and this suspension with a solution of the Acid chloride or anhydride mixed in diethyl ether, acetone or DMF, appropriate at temperatures between about -25 ° and +20 °.

Dioxane derivatives of the formula I (in which one of the groups A1 and / or A2 means a 1,3-dioxane-2,5-diyl group) are expediently by reacting a corresponding aldehyde, for example of the formulas Rl- (Al) m -CHO, R¹- (A¹) m-Z¹-A-Z²-CHO, O = CH- (A¹) m-Z¹-A-Z²- (A²) n- R² or O = CH-R² (or one of its reactive derivatives) with a corresponding one 1,3-diol, for example of the formulas (HOCH2) 2CH- (A1) m-1-Z1 -A-Z2- (A2) n -R2, (HOCH2) 2CH2-R2, R1- (A1) m-1-CH (CH2OH) 2 or R¹- (A¹) m-Z¹-A-Z²-CH (CH2OH) 2 (or one of its reactive derivatives), preferably in the presence of an inert solvent such as benzene or toluene and / or a catalyst, e.g. a strong acid such as sulfuric acid, benzene or p-toluenesulfonic acid, at temperatures between about 20 ° and about 150 °, preferably between 80 and 120 °. As reactive derivatives of the starting materials are primarily suitable Acetals, for example of the formulas R¹- (A¹) m-1CH (OR³) 2, R¹- (A¹) m-Z¹-A-Z²-CH (OR³) 2, (R³O) 2CH- (A¹) m-1-Z¹- A-Z²- (A²) n-R², (R³O) 2-R², R4-CH (OCH2) 2CH- (A¹) m-1-Z¹-A-Z²- (A²) n-R², R4-CH (OCH2) 2CH-R², R¹- (A¹) m-1-CH (CH2O) 2CH-R4 respectively.

R¹- (A¹) m-Z¹-A-Z¹-CH (CH2O) 2CHR4, in which R³ is alkyl with 1 - 4 carbon atoms, two radicals R³ together also alkylene with 2 or 3 carbon atoms and R4 H, alkyl with 1 - mean 4 carbon atoms or phenyl.

The aldehydes and 1,3-diols mentioned and their reactive derivatives are partly known, partly they can be carried out without difficulty using standard procedures organic chemistry from compounds known from the literature. For example are the aldehydes by oxidation of corresponding alcohols or by reduction of the corresponding Carboxylic acids or their derivatives, the diols by reducing the corresponding diesters available.

For the preparation of nitriles of the formula I (in which R1 and / or R2 are CN and / or in which A is substituted by at least one CN group) corresponding acid amides, e.g. those in which instead of the radical X a CONH2 group stands to be dehydrated. The amides are, for example, from corresponding esters or Acid halides available through reaction with ammonia. As dehydrating Suitable agents are, for example, inorganic acid chlorides such as SOCl2, Pol3, PC15, POC13, SO2Cl2, COC12, also P205, P2S5, AlCl3 (e.g. as a double compound with NaCl), aromatic sulfonic acids and sulfonic acid halides. You can do it in the present or the absence of an inert solvent at temperatures between about 0 ° and 150 work; e.g. bases such as pyridine or triethylamine are used as solvents, aromatic hydrocarbons such as benzene, toluene or xylene or amides such as DMF into consideration.

For the preparation of the aforementioned nitriles of the formula I can corresponding acid halides, preferably the chlorides, with sulfamide implement, expediently in an inert solvent such as tetramethylene sulfone Temperatures between about 80 ° and 150 °, preferably at 120 °. According to the usual Work-up can be used to isolate the nitriles directly.

Nitriles of the formula I, in which A is substituted in the 1-position by CN 1,4-Cyclohexylene group means are also obtained by alkylation of acetonitriles Formula II with 1,5-Di-X1 - pentane derivatives of the formula III available. The acetonitrile are, for example, from corresponding halides of the formula R1Al) m-Z1-CH, ul and Metal cyanides obtainable, the compounds III by reducing the corresponding glutaric acid diesters to the corresponding diols (III, X1 = OB) and, if appropriate, implementation of the same with inorganic halides such as SOCl2, HBr or HJ. The acetonitrile becomes appropriate first with a strong base such as NaH, NaNH2, lithium diisopropylamide, lithium piperidide or -2,5-diisopropylpiperidide or K-tert-butoxide into the corresponding carbanion converted, preferably in an inert solvent, for example a hydrocarbon such as toluene, an ether such as THF or dioxane, an amide such as DMF, a sulfoxide such as dimethyl sulfoxide or a mixture of such solvents. After adding III (in which X1 is different from OH) is expediently maintained for 0.5 to 16 hours Temperatures between 0 and 150 °. A conversion of II with III (X1 = OH) succeeds on the other hand, useful in the presence of azodicarboxylic acid esters / triphenylphosphine in THF at temperatures between about -30 ° and +30 °.

In a very analogous manner, nitriles of the formula I, in which A is an in 1- or 4-position by CN-substituted 1,4-cyclohexylene group means the additional can be substituted by 1 - 2 F atoms and / or CN groups, obtainable by a nitrile of the formula IV is reacted with a halide of the formula V. The nitriles of the formula IV are, for example, from corresponding amides of the formula Q1-A3CONH obtainable by dehydration, the halides of the formula V from corresponding Alcohols of the formula Q2-OH.

Ethers of formula I (wherein R¹ and / or R² one through one or two O atoms mean interrupted alkyl chain and / or where Z1 and / or z2 is an -OCH2- or a -CH2O group) are etherified by corresponding hydroxy compounds, preferably corresponding phenols, obtainable, the hydroxy compound being expedient first into a corresponding metal derivative, e.g. by treating with NaOH, KOH, Na2CO3 or K2CO3 into the corresponding alkali metal alcoholate or alkali metal phenate is convicted. This can then with the corresponding alkyl halide, sulfonate or dialkyl sulfate are reacted, advantageously in an inert solvent such as Acetone, DMF or dimethyl sulfoxide or an excess of aqueous or aqueous alcoholic NaOH or KOH at temperatures between about 20 ° and 100 ° For the production of nitriles of the formula I (in which R1 and / or R2 denote CN and / or in which A is replaced by at least a CN group is substituted) can also corresponding chlorine or bromine compounds of the formula I (in which R1 and / or R2 are Cl or Br and / or in which A is represented by at least a Cl or Br atom is substituted) are reacted with a cyanide, expedient with a metal cyanide such as NaCN, KCN or Cu2 (CN) 2, e.g. in the presence of pyridine in an inert solvent such as DMF or N-methylpyrrolidone at temperatures between 20 ° and 200 °.

A base of the formula I can be converted into the associated acid addition salt with an acid be transferred. Inorganic acids can be used for this reaction, e.g. sulfuric acid, nitric acid, hydrohalic acids such as hydrochloric acid or hydrobromic acid, phosphoric acids such as orthophosphoric acid, sulfamic acid, also organic acids1 in particular aliphatic, alicyclic, araliphatic, aromatic or heterocyclic monobasic or polybasic carboxylic, sulfonic or sulfuric acids, e.g. formic acid, acetic acid, propionic acid, pivalic acid, diethylene acetic acid, malonic acid, Succinic acid, pimelic acid, fumaric acid, maleic acid, lactic acid, tartaric acid, xplelic acid, Benzoic acid, salicylic acid, 2- or 3-phenylpropionic acid, citric acid, gluconic acid, Ascorbic acid, nicotinic acid, isonicotinic acid, methane or ethanesulphonic acid, ethanedisulphonic acid, 2-hyaroxyethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, naphthalene-mono- and disulfonic acids, laurylsulfuric acid.

Conversely, it is possible to make a compound from an acid addition salt of the formula I to release the base of the formula I by treatment with a base, e.g. with a strong inorganic base such as KOH or NaOH.

The dielectrics according to the invention consist of 2 to 15, preferably 3 to 12 components, including at least one compound of the formula I. The others Components are preferably selected from nematic or nematogenic Substances, in particular the known substances from the classes of azoxybenzenes, Benzylideneanilines, biphenyls, terphenyls, -phenyl- or cyclohexylbenzoates, cyclohexane-carboxylic acid phenyl- or cyclohexyl esters, phenylcyclohexanes, cyclohexylbiphenyls, cyclohexylcyclohexanes, Cyclohexylnaphthalenes, 1,4-bis-cyclohexylbenzenes, 4,4'-bis-cyclohexylbiphenyls, Phenyl- or cyclohexylpyrimidines, phenyl- or cyclohexyldioxanes, optionally halogenated stilbenes, benzyl phenyl ethers, tolanes and substituted cinnamic acids.

The most important as components of such liquid-crystalline dielectrics Compounds in question can be characterized by the formula VI, R5-A-G-E-R6 VI in which A and E are each a carbo- or heterocyclic ring system that of 1,4-disubstituted benzene and cyclohexane rings, 4,4'-disubstituted Biphenyl, phenylcyclohexane and cyclohexylcyclohexane systems, 2,5-disubstituted Pyrimidine and 1,3-dioxane rings, 2,6-disubstituted naphthalene, di- and tetrahydronaphthalene, Quinazoline and tetrahydroquinazoline formed group, G -CH = CH - CH = CY- -CH = N (O) - C = C- -CH2-CH2 - CO-O- CH2O -CO-S- -CH2-S - CH = N- -COO-Phe-COO-. Or a C-C single bond, Y halogen, preferably chlorine, or -CN, and R5 and R 6 alkyl, Alkoxy, alkanoyloxy or alkoxycarbonyloxy with up to 18, preferably up to 8 Carbon atoms, or one of these radicals also CN, NC, NO2, CF3, F, C1 or Br mean.

In most of these compounds, R5 and R6 are different from one another, one of these radicals is usually an alkyl or alkoxy group. But others too Variants of the intended substituents are common. Lots of such substances or mixtures thereof are available commercially.

The dielectrics according to the invention contain about 0.1 to 100, preferably 10 to 100%, one or more compounds of formula 1.

The dielectrics according to the invention are produced in and of themselves usual way. As a rule, the components are dissolved in one another, expediently at elevated temperature.

With suitable additives, the liquid-crystalline dielectrics be modified according to the invention so that they are in all previously known Types of liquid crystal display elements can be used.

Such additives are known to the person skilled in the art and are detailed in the literature described. For example, electrolyte salts, preferably ethyl dimethyl dodecyl ammonium 4-hexyloxybenzoate, Tetrabutylammonium tetraphenylboranate or complex salts of crown ethers (val. E.g. 1. Haller et al., Mol. Cryst. Liq. Cryst. Volume 24, pages 249-258 (1973)) to improve conductivity, dichroic dyes for the production of colored guest-host systems or substances for changing the dielectric anisotropy, the viscosity and / or the orientation of the nematic phases can be added. Such substances are e.g. in DE-OS 22 09 127, 22 40 864, 23 21 632, 23 38 281, 24 50 088, 26 37 430, 28 53 728 and 29 02 177 described.

The following examples are intended to illustrate the invention without limiting it limit. F. = melting point, K. = clearing point. Above and below denote percentages Weight percent; all temperatures are given in degrees Celsius. "Usual work-up" means: one adds water, extracts with methylene chloride, separates off, dries the organic phase, evaporates and purifies the product by crystallization and / or Chromatography.

Example 1 A solution of 30.1 g of r-1-cyano-1-methoxymethyl-cis-4- (p-methoxybenzoylmethyl) -cyclohexane (available from anisole and cis-4-cyano-4-methoxymethylcyclohexyl-r-1-acetyl chloride in the presence of All3) in 500 ml of TBF, 5 g of 10% of a PdC is applied at 40 ° and 1 bar Hydrogenated up to the uptake of 0.2 mol of H2. It is filtered, evaporated and r-1-cyano-1-methoxymethyl-cis-4- (2-p-methoxyphenylethyl) -cyclohexane is obtained.

Example 2 A solution of 30.4 g of r-1-fluoro-1-pentyl-cis-4- (2-pmethoxyphenylvinyl) -cyclohexane [obtainable by reaction of 4-fluoro-4-pentylcyclohexylmagnesium bromide with p-methoxyphenylacetaldehyde, subsequent hydrolysis to r-1-fluoro-1-pentyl-cis-4- (2-p-methoxyphenyl-1-hydroxyethyl) -cyclohexane and dehydration with p-toluenesulfonic acid in boiling toluene in 600 ml of THF is hydrogenated on 5 g of PdO at 40 ° and 1 bar until 0.1 mol of H2 is absorbed. Man filtered, evaporated and obtained r-l-fluoro-l-pentyl-cis-4- (2-p-methoxyphenylethyl) -cyclohexane.

Analogously, hydrogenation of the corresponding ethylene derivatives gives: r-1-chloro-1-pentyl-cis-4- (2-p-methoxyphenylethyl) -cyclohexane r-1-bromo-1-pentyl-cis-4- (2-p-methoxyphenylethyl) -cyclohexane.

Example 3 A solution of 2.42 g of 1-propyl-4-p-propylphenylcyclohexene is passed at 0 ° HBr (obtainable by reaction of 4-p-propylphenylcyclohexanone with C3H7MgBr, hydrolysis to l-propyl-4-p-propylphenylcyclohexan-1-ol and dehydration) in 50 ml CH2C12, left to stand overnight, worked up as usual and obtained r-1-bromo-1-propyl-cis-4-p-propylphenylcyclohexane.

Analogously, one obtains by adding HCl or HBr to the corresponding Cyclohexenes: r-1-chloro-1-pentyl-cis-4-p-methoxyphenylcyclohexane r-1-bromo-1-pentyl-cis-4-p-methoxyphenylcyclohexane.

Example 4 30.4 g of l-pentyl-4- (trans-4-pentylcyclohexyl) cyclohexene are heated in an autoclave [obtainable by reacting 4- (trans-4-pentylcyclohexyl) cyclohexanone with Pentyl-MgBr, hydrolysis to l-pentyl-4- (trans-4-pentylcyclohexyl) -cyclohexanol and Dehydration], 2.7 g of liquid HCN, 0.1 g of palladium-bis- [2,3-O-isopropylidene-2,3-dihydroxy-1,4-bis (diphenylphosphino) butane] and 100 ml of acetonitrile for 1 hour at 130 °. After cooling, evaporation and more usual Work-up gives r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, F. 28 °, K. 63 analogously obtained by adding HCN to the corresponding Cyclohexene derivatives: r-1-cyano-1-propyl-cis-4- (4-propyl-1-piperidyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (4-Butyl-1-piperidyl) -cyclohexane r-1-Cyano-1-propyl-cis -4- (4-pentyl-1-piperidyl) -cyclohexane r-1-Cyano-1-propyl-cis-4- (4-hexyl-1-piperidyl) -cyclohexane r-1-Cyano-1-propyl-cis-4- (4-heptyl-1-piperidyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-propyl-1-piperidyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-butyl-1-piperidyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-pentyl-1-piperidyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-hexyl-1-piperidyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-heptyl-1-piperidyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-propyl-1-piperidyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-butyl-1-piperidyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (4-pentyl-1-piperidyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (4-hexyl-1-piperidyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-heptyl-1-piperidyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (4-propyl-1-piperidyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (4-butyl-1-piperidyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (4-pentyl-1-piperidyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (4-hexyl-1-piperidyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (4-heptyl-1-piperidyl) -cyclohexane r-1-Cyano-1-heptyl-cis-4- (4-propyl-1-piperidyl) -cyclohexane r-1-Cyano-1-heptyl-cis-4- (4-butyl-1-piperidyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (4-pentyl-1.piperidyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (4-hexyl-1-piperidyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (4-heptyl-1-piperidyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (4-propyl-bicyclo [2 ' 2,2] octyl) cyclohexane r -1-cyano-1-propyl-cis -4- (4-butyl-bicyclo [2,2,2loctyl) -cyclohexane rl-cyano-1-propyl-cis-4- (4-pentyl-bicyclo [2,2,2loctyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (4-hexyl-bicyclo [2, 2.2] octyl) cyclohexane r -1-Cyano-1-propyl-cis -4- (4-heptyl-bicyclo [2.2.2] octyl) -cyclohexane r-1-Cyano-1-butyl-cis -4- (4-propyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-Cyano-1-butyl-cis -4- (4-butyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (4-pentyl bicyclo [2,2,2] octyl) cyclohexane rl-cyano-1-butyl-cis-4- (4-hexyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (4-heptyl-bicyclo [2,2,2] octyl) cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-propyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-butyl bicyclo [2,2,2] octyl) cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-pentyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (4-hexyl bicyclo [2,2,2] octyl) cyclohexane r-1-cyano-1-pentyl-cis-4- (4-heptyl-bicyclo [2,2,2] -octyl) -cyclohexane rl-cyano-1-hexyl-cis-4- (4-propyl-bicyclo [2,2,2] octyl) cyclohexane r-1-Cyano-1-hexyl-cis-4- (4-butyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (4-pentyl bicyclo [2,2,2] octyl) cyclohexane rl-cyano-1-hexyl-cis-4- (4-hexyl-bicyclo [2,2,2] -octyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (4-heptyl-bicyclo [2,2,23-octyl) cyclohexane r-l-cyano-1-heptyl-cis-4- (4-propyl-bicyclo [2.2.2] octyl) -cyclohexane r -1-cyano-1-heptyl-cis -4- (4-butyl-bicyclo [2.2.2] octyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (4-pentyl-bicyclo [2.2.2] octyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (4-hexyl- bicyclo [2,2,2] octyl) cyclohexane r-1-Cyano-1-heptyl-cis-4- (4-heptyl-bicyclo [2,2,2] -octyl) -cyclohexane.

Example 5 17 g of trans-4-propylcyclohexanecarboxylic acid are boiled for 1 hour. with 24 g of SOCl2, evaporated, the crude acid chloride obtained dissolves in 150 ml of toluene, mixed with 8 ml of pyridine and 16.7 g of cis-4-cyano-4-propylcyclohexanol (available by alkylation of 4-cyanocyclohexanol) and boiled for 2 hours. After cooling down and Customary work-up gives trans-4-propylcyclohexanecarboxylic acid (cis-4-cyano-4-propylcyclohexyl ester).

In an analogous manner, esterification of the corresponding acids gives: trans-4-propylcyclohexanecarbons acid (cis-4-cyano-4-butylcyclohexyl ester) trans-4-propylcyclohexanecarboxylic acid (cis-4-cyano-4-pentylcyclohexyl ester) trans-4-propylcyclohexanecarboxylic acid (cis-4-cyano-4-hexylcyclohexyl ester) trans-4-propylcyclohexanecarboxylic acid (cis-4-cyano-4-heptylcyclohexyl ester) trans-4-butylcyclohexanecarboxylic acid (cis-4-cyano-4-propylcyclohexyl ester) trans-4-butylcyclohexanecarboxylic acid (cis-4-cyano-4-butylcyclohexyl ester) trans-4-butylcyclohexanecarboxylic acid (cis-4-cyano-4-pentylcyclohexyl ester) trans-4-butylcyclohexanecarboxylic acid (cis-4-cyano-4-hexylcyclohexyl ester) trans-4-butylcyclohexanecarboxylic acid (cis-4-cyano-4-heptylcyclohexyl ester) trans-4-pentylcyclohexanecarboxylic acid (cis-4-cyano-4-propylcyclohexyl ester) trans-4-pentylcyclohexanecarboxylic acid (cis-4-cyano-4-butylcyclohexyl ester) trans-4-pentylcyclohexanecarboxylic acid (cis-4-cyano-4-pentylcyclohexyl ester) trans-4-pentylcyclohexanecarboxylic acid (cis-4-cyano-4-hexylcyclohexyl ester) trans-4-pentylcyclohexanecarboxylic acid (cis-4-cyano-4-heptylcyclohexyl ester) trans-4-Hexylcyclohexanecarboxylic acid (cis-4-cyano-4-propylcyclohexyl ester) trans-4-Hexylcyclohexanecarboxylic acid (cis-4-cyano-4-butylcyclohexyl ester) trans-4-hexylcyclohexanecarboxylic acid (cis-4-cyano-4-pentylcyclohexyl ester) trans-4-Hexylcyclohexanecarboxylic acid (cis-4-cyano-4-hexylcyclohexyl ester) trans-4-Hexylcyclohexanecarboxylic acid (cis-4-cyano-4-heptylcyclohexyl ester) trans-4-heptylcyclohexanecarboxylic acid (cis-4-cyano-4-propylcyclohexyl ester) trans-4-heptylcyclohexanecarboxylic acid (cis-4-cyano-4-butylcyclohexyl ester) trans-4-heptylcyclohexanecarboxylic acid (cis-4-cyano-4-pentylcyclohexyl ester) trans-4-heptylcyclohexanecarboxylic acid (cis-4-cyano-4-hexylcyclohexyl ester) trans-4-heptylcyclohexanecarboxylic acid (cis-4-cyano-4-heptylcyclohexyl ester) cis-4-cyano-4-propylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (trans-4-butylcyclohexyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (trans-4-pentylcyclohexyl ester) cis-4-cyano-4-propylcyclohexanecarboxylic acid (trans-4-hexylcyclohexyl ester) cis-4-cyano-4-propylcyclohexanecarboxylic acid (trans-4-heptylcyclohexyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (trans-4-butylcyclohexyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (trans-4-pentylcyclohexyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (trans-4-hexylcyclohexyl ester) cis-4-cyano-4-butylcyclohexanecarboxylic acid (trans-4-heptylcyclohexyl ester) cis-4-cyano-4-pentylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (trans-4-butylcyclohexyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (trans-4-pentylcyclohexyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (trans-4-hexylcyclohexyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (trans-4-heptylcyclohexyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (trans-4-butylcyclohexyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (trans-4-pentylcyclohexyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (trans-4-hexylcyclohexyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (trans-4-heptylcyclohexyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (trans-4-butylcyclohexyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (trans-4-pentylcyclohexyl ester) cis-4-cyano-4-heptylcyclohexanecarboxylic acid (trans-4-hexylcyclohexyl ester) cìs-4-cyano-4-heptylcyclohexanecarboxylic acid (trans-4-heptylcyclohexyl ester) p-methoxybenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-methoxybenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Methoxybenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Methoxybenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Methoxybenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-ethoxybenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Ethoxybenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-ethoxybenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-ethoxybenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-ethoxybenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-Propoxybenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Propoxybenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Propoxybenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Propoxybenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Propoxybenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-Butoxybenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Butoxybenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Butoxybenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Butoxybenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Butoxybenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-Propylbenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Propylbenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Propylbenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Propylbenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Propylbenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-Butylbenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Butylbenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Butylbenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Butylbenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Butylbenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) p-Pentylbenzoic acid (cis-4-cyano-4-propylcyclohexyl ester) p-Pentylbenzoic acid (cis-4-cyano-4-butylcyclohexyl ester) p-Pentylbenzoic acid (cis-4-cyano-4-pentylcyclohexyl ester) p-Pentylbenzoic acid (cis-4-cyano-4-hexylcyclohexyl ester) p-Pentylbenzoic acid (cis-4-cyano-4-heptylcyclohexyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-methoxyphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-propoxyphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-butoxyphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-propylphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-butylphenyl ester) cis-4-Cyano-4-propylcyclohexanecarboxylic acid (p-pentylphenyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (p-methoxyphenyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (p-propoxyphenyl ester) cis-4-cyano-4-butylcyclohexanecarboxylic acid (p-butoxyphenyl ester) cis-4-cyano-4-butylcyclohexanecarboxylic acid (p-propylphenyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (p-butylphenyl ester) cis-4-Cyano-4-butylcyclohexanecarboxylic acid (p-pentylphenyl ester) cis-4-cyano-4-pentylcyclohexanecarboxylic acid (p-methoxyphenyl ester) vCis-4-cyano-4-pentylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (p-propoxyphenyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (p-butoxyphenyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (p-propylphenyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (p-butylphenyl ester) cis-4-Cyano-4-pentylcyclohexanecarboxylic acid (p-pentylphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-methoxyphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-propoxyphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-butoxyphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-propylphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-butylphenyl ester) cis-4-Cyano-4-hexylcyclohexanecarboxylic acid (p-pentylphenyl ester) cis-4-cyano-4-heptylcyclohexanecarboxylic acid (p-methOxyphenyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (p-propoxyphenyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (p-butoxyphenyl ester) cis-4-Cyano-4-heptylcyclohexanecarboxylic acid (p-propylphenyl ester) cis -4-Cyano-4-heptylcyclohexanecarboxylic acid (p-butylphenyl ester) cis -4-Cyano-4-heptylcyclohexanecarboxylic acid (p-pentylphenyl ester).

Example 6 A mixture of 1.2 g of 2-propylpropane-1,3-diol, 1.79 g of 1-cyano-1-propyl-4-formyl-cyclohexane (obtainable by alkylating 1-cyano-4-formylcyclohexane with propyl bromide), 0.01 g of p-toluenesulfonic acid and 15 ml of toluene are boiled on a water separator for 3 hours, cooled, washed with water and evaporated. 1-r-Cyano-1-propyl-cis-4- (trans-5-propyl-1,3-dioxan-2-yl) -cyclohexane is obtained.

By reacting the corresponding aldehydes with, one obtains analogously the corresponding diols: 1-r-cyano-1-propyl-cis-4- (trans-5-butyl-1,3-dioxan-2-yl) -cyclohexane l-r-cyano-l-propyl-cis-4- (trans-5-pentyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-propyl-cis-4- (trans-5-hexyl-1,3-dioxan-2-yl) -cyclohexane l-r-cyano-l-propyl-cis-4- (trans-5-heptyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-butyl-cis-4- (trans-5-propyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-1-butyl-cis-4- (trans- 5-butyl-1,3-dioxan-2-yl) cyclohexane lr-cyano-1-butyl-cis-4- (trans-5-pentyl-1,3-dioxan-2-yl) -cyclohexane lr-cyano-l-butyl-cis-4- (trans-5-hexyl- 1,3-dioxan-2-yl) cyclohexane 1-r-cyano-1-butyl-cis-4- (trans-5-heptyl-1,3-dioxan-2-yl) -cyclohexane l-r-cyano-l-pentyl-cis-4- (trans-5-propyl-1, 3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-pentyl-cis-4- (trans-5-butyl-1, 3-dioxan-2-yl) -cyclohexane l-r-cyano-l-pentyl-cis-4- (trans-5-pentyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-pentyl-cis-4- (trans-5-hexyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-1-pentyl-cis-4- (trans- 5-heptyl-1,3-dioxan-2-yl) cyclohexane 1-r-cyano-l-hexyl-cis-4- (trans-5-propyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-hexyl-cis-4- (trans- 5-butyl-1,3-dioxan-2-yl) -cycl ohexane 1-r-cyano-1-hexyl-cis-4- (trans-5-pentyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-1-hexyl-cis-4- (trans -5-hexyl-1,3-dioxan-2-yl) cyclohexane 1-r-Cyano-1-hexyl-cis-4- (trans-5-heptyl-1,3-dioxan-2-yl) -cyclohexane l-r-cyano-1-heptyl-cis-4- (trans-5-propyl-1,3-dioxan-2-yl) -cyclohexane lr-cyano-1-heptyl-cis-4- (trans-5-butyl-1,3-dioxan-2-yl) -cyclohexane 1-r-cyano-l-heptyl-cis-4- (trans-5- propyl-1,3-dioxan-2-yl) cyclohexane lr-cyano-l-heptyl-cis-4- (trans-5-pentyl-1,3-dioxan-2-yl) -cyclohexane lr-cyano-1-heptyl-cis-4- (trans-5-hexyl- 1,3-dioxan-2-yl) cyclohexane 1-r-Cyano-1-heptyl-cis-4- (trans-5-heptyl-1,3-dioxan-2-yl) -cyclohexane.

Example 7 A solution of 34.9 g of r-1-carbamoyl-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) cyclohexane (obtainable from the acid chloride with NH3) in 500 ml DMF is stirred at 50 ° 65 g of POCl3 were added dropwise. After stirring for a further hour, it is poured on ice, works up as usual and receives r-l-cyano-l-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, F. 28 °, K. 63 Example 8 A solution of 36.9 g of l-pentyl-cis-4- (trans-4-pentylcyclohexyl ) -cyclohexane-r-1-carbonyl chloride [obtainable by reacting 4- (4-pentylcyclohexyl ) -cyclohexanone with pentyl-Li and subsequent hydrolysis to 1-pentyl-4- (4-pentylcyclohexyl ) -cyclohexanol, reaction with K, then with CO2 to form 1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane-r-l-carboxylic acid and reaction with SOCl2] and 8 g of sulfamide in 500 ml of tetramethylene sulfone is 4 hours. heated to 120 °, evaporated and worked up as usual. One obtains r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, F. 28, K. 63 °.

Example 9 A solution of 26.3 g of 4'-pentyl-biphenylyl-4-acetonitrile [F. 80 °, K. -10 0; obtainable from 4-acetyl-4'-pentyl-biphenyl via 4'-pentyl-biphenylyl-4-acetic acid (F. 160 0) and the corresponding amide (F. 185 0)] in 150 ml of dimethyl sulfoxide with stirring with 6 g of NaH. (50% in paraffin), then with a solution of 25.3 g 1,5-dibromopentane in 50 ml of dioxane is added; the temperature is maintained by cooling below 35 °. The mixture is stirred for a further 2 hours, isopropanol is added and the process is carried out as usual on. 1-Cyano-1- (4'-pentyl-4-biphenylyl) -cyclohexane, mp 64, is obtained analogously from the corresponding acetonitriles and the corresponding 1,5-dibromopentanes: l-r-cyano-l- (trans-4-propylcyclohexyl3-cis-4-propylcyclohexane l-r-cyano-l- (trans-4-propylcyclohexyl) -cis-4-butylcyclohexane 1-r-Cyano-1- (trans-4-propylcyclohexyl) -cis-4-pentylcyclohexane 1-r-Cyano-1- (trans-4-propylcyclohexyl) -cis-4-hexylcyclohexane l-r-cyano-l- (trans-4-propylcyclohexyl) -cis-4-heptylcyclohexane 1-r-cyano-1- (trans-4-butylcyclohexyl ) -cis-4-propylcyclohexane l-r-cyano-l- (trans-4-butylcyclohexyl) -cis-4-butylcyclohexane 1-r-cyano-1- (trans-4-butylcyclohexyl) -cis-4-pentylcyclohexane 1-r-cyano-1- (trans-4-butylcyclohexyl) -cis-4-hexylcyclohexane 1-r-Cyano-1- (trans-4-butylcyclohexyl) -cis-4-heptylcyclohexane l-r-Cyano-1- (trans-4-pentylcyclohexyl) -cis-4-propylcyclohexane l-r-cyano-l- (trans-4-pentylcyclohexyl) -cis-4-butylcyclohexane 1-r-cyano-1- (trans-4-pentylcyclohexyl ) -cis-4-pentylcyclohexane 1-r -cyano-1- (trans-4-pentylcyclohexyl) -cis-4-hexylcyclohexane l-r-cyano-l- (trans-4-pentylcyclohexyl) -cis-4-heptylcyclohexane l-r-cyano-l- (trans-4-hexylcyclohexyl) -cis-4-propylcyclohexane l-r-Cyano-1- (trans-4-hexylcyclohexyl) -cis-4-butylcyclohexane 1-r-Cyano-1- (trans-4-hexylcyclohexyl ) -cis-4-pentylcyclohexane 1-r-cyano-1- (trans-4-hexylcyclohexyl) -cis-4-hexylcyclohexane 1-r-Cyano-1- (trans-4-hexylcyclohexyl) -cis-4-heptylcyclohexane l-r-Cyano-1- (trans-4-heptylcyclohexyl) -cis-4-propylcyclohexane l-r-Cyano-1- (trans-4-heptylcyclohexyl) -cis-4-butylcyclohexane 1-r-Cyano-1- (trans-4-heptylcyclohexyl) -cis-4-pentylcyclohexane 1-r-cyano-1- (trans-4-heptylcyclohexyl) -cis-4-hexylcyclohexane 1-r-cyano-1- (trans-4-heptylcyclohexyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (p-methoxyphenyl) -cis-4-propylcyclohexane r-1-Cyano-1- (p-methoxyphenyl) -cis-4-butylcyclohexane r-l-cyano-1- (p-methoxyphenyl) -cis -4-pentylcyclohexane r-l-cyano-1- (p-methoxyphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-methoxyphenyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (p-ethoxyphenyl) -cis-4-propylcyclohexane r-l-cyano-l- (p-ethoxyphenyl) -cis-4-butylcyclohexane r-1-cyano-l- (p-ethoxyphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-ethoxyphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-ethoxyphenyl) -cis-4-heptylcyclohexane r-1-cyano-1- (p-propoxyphenyl) -cis-4-propylcyclohexane r-1-cyano-1- (p-propoxyphenyl) -cis-4-butylcyclohexane r-1-Cyano-1- (p-propoxyphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-propoxyphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-propoxyphenyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (p-butoxyphenyl) -cis-4-propylcyclohexane r-1-cyano-1- (p-butoxyphenyl) -cis-4-butyocyclohexane r-1-cyano-1- (p-butoxyphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-butoxyphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-butoxyphenyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (p-propylphenyl) -cis-4-propylcyclohexane r-1-Cyano-1- (p-propylphenyl) -cis-4-butylcyclohexane r-1-Cyano-1- (p-propylphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-propylphenyl) -cis-4-hexylcyclohexane r-1-cyano-1- (p-propylphenyl) -cis-4-heptylcyclohexane r-l-cyano-l- (p-butylphenyl) -cis-4-propylcyclohexane r-1-Cyano-1- (p-butylphenyl) -cis-4-butylcyclohexane r-1-Cyano-1- (p-butylphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-butylphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-butylphenyl) -cis-4-heptylcyclohexane r-1-cyano-1- (p-pentylphenyl) -cis-4-propylcyclohexane r- l-cyano-1- (p-pentylphenyl) -cis-4-butylcyclohexane r-1-Cyano-1- (p-pentylphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (p-pentylphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (p-pentylphenyl) -cis -4-heptylcyclohexane r-1-Cyano-1- (2-fluoro-4-methoxyphenyl) -cis-4-propyl cyclohexane r-1-cyano-1- (2-fluoro-4-methoxyphenyl) -cis-4-butylcyclohexane r-1-cyano-1- (2-fluoro-4-methoxyphenyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-fluoro-4-methoxyphenyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (2-fluoro-4-methoxyphenyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (2,3,5,6-tetrafluoro-4-methoxyphenyl) -cispropylcyclohexane r-1-Cyano-1- (2,3,5,6-tetrafluoro-4-methoxyphenyl) -cisbutylcyclohexane r-1-Cyano-1- (2,3,5,6-tetrafluoro-4-methoxyphenyl) -cispentylcyclohexane r-1-Cyano-1- (2,3,5,6-tetrafluoro-4-methoxyphenyl) -cishexylcyclohexane r-1-Cyano-1- (2,3,5,6-tetrafluoro-4-methoxyphenyl) -cisheptylcyclohexane r-1-cyano-1-p-fluorophenyl-cis-4-propylcyclohexane r-l-cyano-l-p-chlorophenyl-cis-4-propylcyclohexane r-l-cyano-1-p-bromophenyl-cis-4-propylcyclohexane r-1-cyano-l- (trans-5-propyl-1,3-dioxan-2-yl) -cis-4-propylcyclohexane rl-cyano-l- (trans-5-propyl-1,3-dioxane 2-yl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-5-propyl-1,3-dioxan-2-yl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-5-propyl-1,3- dioxan-2-yl) -cis-4-hexylcyclohexane r-1-cyano-1- (trans-5-propyl-1,3-dioxan-2-yl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-5-butyl-1,3- dioxan-2-yl) -cis-4-propylcyclohexane r-l-cyano-l- (trans-5-butyl-1,3-dioxan-2-yl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-5-butyl-1, 3-dioxan-2-yl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-5-butyl-1,3-dioxan-2-yl ? -cis -4-hexylcyclohexane r-l-cyano-l- (trans-5-butyl-1,3-dioxan-2-yl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-5-pentyl-1,3-dioxan-2-yl) -cis-4-propylcyclohexane rl-cyano-1- (trans-5-pentyl-1,3-dioxane 2-yl) -cis-4-butylcyclohexane rl-cyano-1- (trans-5-pentyl-1,3-dioxan-2-yl) -cis-4-pentylcyclohexane rl-cyano-l- (trans-5-pentyl-1,3-dioxane-2- yl) -cis-4-hexylcyclohexane r-1-cyano-1- (trans-5-pentyl-1, 3-dioxan-2-yl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-5-hexyl-1,3-dioxan-2-yl) -cis-4-propylcyclohexane r-1-cyano-1- (trans-5-hexyl-1,3-dioxan-2-yl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-5-hexyl-1,3- dioxan-2-yl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-5-hexyl-1,3-dioxan-2-yl) -cis-4-hexylcyclohexane r-1-cyano-1- (trans-5-hexyl-1,3- dioxan-2-yl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-5-heptyl-1,3-dioxan-2-yl) -cis-4-propylcyclohexane r-1-cyano-1- (trans-5-heptyl-1,3- dioxan-2-yl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-5-heptyl-1,3-dioxan-2-yl) -cis-4-pentylcyclohexane r-1-cyano-l- (trans-5-heptyl-1,3- dioxan-2-yl) -cis-4-hexylcyclohexane r-1-Cyano-1- (trans-5-heptyl-1,3-dioxan-2-yl) -cis-4-heptylcyclohexane r-1-Cyano-1- (5-propyl-2-pyrimidyl) -cis -4-propylcyclohexane r-1-Cyano-1- (5-propyl-2-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (5-propyl-2-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (5-propyl-2-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (5-propyl-2-pyrimidyl) -cis-4-heptylcyclohexane r-1-cyano-1- (5-butyl-2-pyrimidyl ) -cis-4-propylcyclohexane r-1-cyano-1- (5-butyl-2-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (5-butyl-2-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (5-butyl-2-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (5-butyl-2-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (5-pentyl-2-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (5-pentyl-2-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (5-pentyl-2-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (5-pentyl-2-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (5-pentyl-2-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (5-hexyl-2-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (5-hexyl-2-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (5-hexyl-2-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (5-hexyl-2-pyrimidyl) -cis-4-hexylcyclohexane r-1-cyano-1- (5-hexyl-2-pyrimidyl) -cis-4-heptylcyclohexane r-1-cyano-1- (5-heptyl-2-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (5-heptyl-2-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (5-heptyl-2-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (5-heptyl-2-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (5-heptyl-2-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (2-propyl-5-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (2-propyl-5-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (2-propyl-5-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-propyl-5-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (2-propyl-5-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (2-butyl-5-pyrimidyl ) -cis -4-propylcyclohexane r-1-cyano-1- (2-butyl-5-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (2-butyl-5-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-butyl-5-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (2-butyl-5-pyrimidyl) -cis-4-heptylcyclohexane r-1-cyano-1- (2-pentyl-5-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (2-pentyl-5-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (2-pentyl-5-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-pentyl-5-pyrimidyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (2-pentyl-5-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (2-hexyl-5-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (2-hexyl-5-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (2-hexyl-5-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-hexyl-5-pyrimidyl ) -cis -4-hexylcyclohexane r-1-cyano-1- (2-hexyl-5-pyrimidyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (2-heptyl-5-pyrimidyl) -cis-4-propylcyclohexane r-1-Cyano-1- (2-heptyl-5-pyrimidyl) -cis-4-butylcyclohexane r-1-Cyano-1- (2-heptyl-5-pyrimidyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (2-heptyl-5-pyrimidyl) -cis-4-hexylcyclohexane r-1-cyano-1- (2-heptyl-5-pyrimidyl) -cis-4-heptylcyclohexane.

Example 10 A solution of 5.22 is added dropwise with stirring at -20 ° g of diethyl azodicarboxylate in 10 ml of THF to a solution of 7.86 g of triphenylphosphine in 200 ml of THF; then 1.48 g of 3-methoxymethyl-1,5-pentanediol and 2.09 g of cyanoacetic acid (4-propylcyclohexyl ester) in 40 ml of THF were added dropwise. One stirs 24 Hours.

at -20 °, another 24 hours at 0, another 24 hours

at 20 °, evaporated, worked up as usual and obtained 1-cyano-trans-4-methoxymethylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester).

Analogously, from the corresponding cyanoacetic acid esters and the corresponding glycols: 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester) l-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (trans-4-butylcyclohexyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (trans-4-pentylcyclohexyl ester) I-cyano-trans-4-propylcyclohexane-r- 1 -carboxylic acid (trans-4-hexylcyclohexyl ester) l-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (trans-4-heptylcyclohexyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-methoxyphenyl ester) l-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-ethoxyphenyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-propoxyphenyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-butoxyphenyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-propylphenyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-butylphenyl ester) 1-cyano-trans-4-propylcyclohexane-r-1-carboxylic acid (p-pentylphenyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (trans-4-butylcyclohexyl ester) l-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (trans-4-pentylcyclohexyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (trans-4-hexylcyclohexyl ester) l-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (trans-4-heptylcyclohexyl ester) l-cyano-trans-4-butylcyclohexane-r-l-carboxylic acid (p-methoxyphenyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (p-ethoxyphenyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (p-propoxyphenyl ester) l-cyano-trans-4-butylcyclohexane-r-l-carboxylic acid (p-butoxyphenyl ester) 1-cyano-trans-4-butylcyclohexane-r-l-carboxylic acid (p-propylphenyl ester) l-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (p-butylphenyl ester) 1-cyano-trans-4-butylcyclohexane-r-1-carboxylic acid (p-pentylphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester) l-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (trans-4-butylcyclohexyl ester) l-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (trans-4-pentylcyclohexyl ester) l-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid-Itrans-4-hexylcyclohexyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (trans-4-heptylcyclohexyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-methoxyphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-ethoxyphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-propoxyphenyl ester) l-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-butoxyphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-propylphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-butylphenyl ester) 1-cyano-trans-4-pentylcyclohexane-r-1-carboxylic acid (p-pentylphenyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (trans-4-butylcyclohexyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (trans-4-pentylcyclohexyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (trans-4-hexylcyclohexyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (trans-4-heptylcyclohexyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-methoxyphenyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-ethoxyphenyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-propoxyphenyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-butoxyphenyl ester) 1-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-propylphenyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-butylphenyl ester) l-cyano-trans-4-hexylcyclohexane-r-1-carboxylic acid (p-pentylphenyl ester) 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (trans-4-propylcyclohexyl ester) 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (trans-4-butylcyclohexyl ester) 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (trans-4-pentylcyclohexyl ester) l-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (trans-4-hexylcyclohexyl ester) l-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (trans-4-heptylcyclohexyl ester) l-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-methoxyphenyl ester) l-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-ethoxyphenyl ester) l-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-propoxyphenyl ester) 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-butoxyphenyl ester) 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-propylphenyl ester) 1-cyano-trans-4-heptylcyclohexane-r-l-carboxylic acid (p-butylphenyl ester), 1-cyano-trans-4-heptylcyclohexane-r-1-carboxylic acid (p-pentylphenyl ester).

Example 11 23.3 g of trans, trans-4-cyano-4'-propylcyclohexylcyclohexane are dissolved and 41 g of butyl bromide in 70 ml of toluene, mixed with 4.3 g of NaNH2 (50% in toluene) and cooks for 5 hours. Customary work-up gives r-1-cyano-1-butyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane, F. 28, K. 28.5 °.

Analogously, by alkylating corresponding nitriles: r-1-cyano-1-methyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane is obtained r-1-Cyano-1-methyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-Cyano-1-methyl-cis-4- (trans-4-butylcyohexyl) -cyclohexane r-1-Cyano-1-methyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-Cyano-1-methyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-Cyano-1-methyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-cyano-1-ethyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane, F. 41 r-1-Cyano-1-ethyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-Cyano-1-ethyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-1-cyano-1-ethyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-cyano-1-ethyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-ethyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-methylcyclohexyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-l-propyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, m.p. 32 °, K. 13 r-1-cyano-1-propyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane, M. 31 °, K. 27 r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, F. 32 °, K. 42 r-1-cyano-1-propyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane, F. 38 °, K. 49 rl-cyano-l-propyl-cis-4- (trans-4-octylcyclohexyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-nonylcyclohexyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-decylcyclohexyl) cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-methylcyclohexyl) cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-octylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-nonylcyclohexyl) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-decylcyclohexyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-methylcyclohexyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, m.p. 39.5 °, K. 48.5 r-1-cyano-1-pentyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane, m.p. 28 °, K. 63 r-1-Cyano-1-pentyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (trans-4-octylcyclohexyl) -cyclohexane r-1-cyano-l-pentyl-cis-4- (trans-4-nonylcyclohexyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-decylcyclohexyl) -cyclohexane r-1-Cayan-1-hexyl-cis-4- (trans-4-methylcyclohexyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, m.p. 17 °, K. 55 rl-Cyano-1-hexyl-cis-4- (trans-4-butylcyclohexyl ) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-heptylcyclohesyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-octylcyclohexyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-nonylcyclohexyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-decylcyclohexyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-methylcyclohexyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-Cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane, m.p. 22 °, K. 56 r-1-cyano-1-heptyl-cis-4- (trans-4-butylcyclohexyl) cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-pentylcycloheXyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-heptylcyclohesyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-octylcyclohexyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-nonylcyclohexyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-decylcyclohexane) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-octyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-hexylcyclohexyl) cyclohexane r-1-cyano-1-nonyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-cyano-1-decyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-1-decyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-cyano-1-decyl-cis-4- (trans-4-butylcyclohexyl) -cyclohexane r-l-cyano-l-decyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-l-cyano-1-decyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-decyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-cyano-1-methoxymethyl-cis-4- (trans-4-ethylcyclohexyl) -cyclohexane r-1-cyano-1-methoxymethyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane r-1-Cyano-1-methoxymethyl-cis-4- (trans-4-butyAcyclohexyl) -cyclohexane r-1-Cyano-1-methoxymethyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-cyano-1-methoxymethyl-cis-4- (trans-4-hexylcyclohexyl) -cyclohexane r-1-cyano-1-methoxymethyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane r-1-Cyano-1- (2,5-dioxahexyl) -cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-Cyano-1-pentyl-2,2-difluoro-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane r-1-Cyano-1-pentyl-cis-4-p-methoxyphenyl-cyclohexane r -1-Cyano-1- [2- (trans -4-propylcyclohexyl) -ethyl] -cis -4-propylcyclohexane rl -cyano-1- [2- (trans-4-propylcyclohexyl) -ethyl] -cis -4 -butylcyclohexane r -1-Cyano-1- [2- (trans -4-propylcyclohexyl) -ethyl] -cis -4-pentylcyclohexane rl -cyano-1- [2- (trans -4-propylcyclohexyl) -ethyl] -cis -4 -hexylcyclohexane r-1-Cyano-1- [2- (trans-4-propylcyclohexyl) -ethyl] -cis -4-heptylcyclohexane r-1-Cyano-1- [2- (trans-4-butylcyclohexyl) -ethyl] -cis -4-propylcyclohexane r-1-Cyano-1- [2- (trans-4-butylcyclohexyl) -ethyl] -cis-4-butylcyclohexane r-1-Cyano-1- [2- (trans-4-butylcyclohexyl) -ethyl] - cis -4-pentylcyclohexane r-1-cyano-1- [2- (trans-4-butylcyclohexyl) -ethyl] -cis-4-hexylcyclohexane r-1-cyano-1-t2- (trans-4-butylcyclohexyl) -ethyl] -cis- 4-heptylcyclohexane r-1-Cyano-1- [2- (trans-4-pentylcyclohexyl) -ethyl] -cis-4-propylcyclohexane r-1-Cyano-1- [2- (trans-4-pentylcyclohexyl) -ethyl] -cis -4-butylcyclohexane r-1-Cyano-1- [2- (trans -4-pentylcyclohexyl) -ethyl] -cis-4-pentylcyclohexane r-1-Cyano-1- [2- (trans -4-pentylcyclohexyl) -ethyl] -cis-4-hexylcyclohexane rl-Cyano-1- [2- (trans -4-pentylcyclohexyl) -ethyl] -cis -4-heptylcyclohexane r-1-Cyano-1- [2- (trans-4-hexylcyclohexyl) -ethyl] -cis -4 -propylcyclohexane r-1-cyano-1- [2- (trans-4-hexylcyclohexyl) -ethyl] -cis-4-butylcyclohexane rl-cyano-1- / 2- (trans-4-hexylcyclohexyl) -ethyll-cis-4- pentylcyclohexane rl-Cyano-1- [2- (trans -4-hexylcyclohexyl) -ethyl] -cis -4-hexylcyclohexane r-1-Cyano-1- [2- (trans-4-hexylcyclohexyl) -ethyl] -cis -4 -heptylcyclohexane r-1-Cyano-1- [2- (trans-4-heptylcyclohexyl) -ethyl] -cis-4-propylcyclohexane r-1-Cyano-1- [2- (trans-4-heptylcyclohexyl) -ethyll-cis -4-butylcyclohexane r-1-Cyano-1- [2- (trans-4-heptylcyclohexyl) -ethyl] -cis-4-pentylcyclohexane r-1-Cyano-1- [2- (trans-4-heptylcyclohexyl) -ethyl] -cis -4-hexylcyclohexane r-1-Cyano-1- [2- (trans-4-heptylcyclohexyl) -ethyll-cis-4-heptylcyclohexane r-1-Cyano-1-propyl-cis-4- [2- (trans-4-propylcyclohexyl) ethyl] cyclohexane r-1-Cyano-1-propyl-cis-4- [2- (trans-4-butylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-propyl-cis-4- [2- (trans-4 pentylcyclohexyl) ethyl] cyclohexane r -1-cyano-1-propyl-cis -4- [2- (trans -4-hexylcyclohexyl) ethyl] cyclohexane r -1-cyano-1-propyl-cis -4- [2- (trans -4-heptylcyclohexyl) -ethyl] -cyclohexane r -1-cyano-1-butyl-cis -4- [2- (trans -4 propylcyclohexyl) ethyl] cyclohexane r-1-Cyano-1-butyl-cis-4- [2- (trans-4-butylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-butyl-cis-4- [2- (trans-4 pentylcyclohexyl) ethyl] cyclohexane r -1-Cyano-1-butyl-cis -4- [2- (trans -4-hexylcyclohexyl) -ethyl] -cyclohexane r -1-cyano-1-butyl-cis -4- [2- (trans -4 -heptylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-pentyl-cis-4- [2- (trans-4-propylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-pentyl-cis-4- [2- (trans-4 -butylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-pentyl-cis-4- [2- (trans-4-pentylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-pentyl-cis-4- [2- (trans-4 -hexylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-pentyl-cis-4- [2- (trans-4-heptylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-hexyl-cis-4- [2- (trans-4 propylcyclohexyl) ethyl] cyclohexane r-1-Cyano-1-hexyl-cis-4- [2- (trans-4-butylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-hexyl-cis-4- [2- (trans-4 pentylcyclohexyl) ethyl] cyclohexane r-1-Cyano-1-hexyl-cis-4- [2- (trans-4-hexylcyclo hexyl) ethyl] cyclohexane r-1-cyano-1-hexyl-cis-4- [2- (trans-4-heptylcyclohexyl) -ethyl] -cyclohexane r -1-cyano-1-heptyl-cis-4- [2- (trans-4-propylcyclohexyl) -ethyl] -cyclohexane r-1-cyano-1-heptyl-cis-4- [2- (trans-4-butylcyclohexyl) -ethyl] -cyclohexane r-1-cyano-1-heptyl-cis-4- [2- (trans -4-pentylcyclohexyl) -ethyl] -cyclohexane r -1-cyano-1-heptyl-cis -4- [2- (trans-4-hexylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-heptyl-cis-4- [2- (trans-4-heptylcyclohexyl) -ethyl] -cyclohexane r-1-Cyano-1-propyl-cis-4- (trans-4-propylcyclohexyl) -ylmethoxy) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-butylcyclohesylmethoxy) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-hexylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-propylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-butylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-pentylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-hexylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-butyl-cis-4- (trans-4-heptylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-pentyl-cis-4- (trans-4-propylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-butylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-hexylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-pentyl-cis-4 - (. trans-4-heptylcycloheXylmethoxy) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (trans-4-propylcyclohexylmethoxy) -cyclohexane r-1-Cyano-1-hexyl-cis-4- (trans-4-butylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-pentylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-hexylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-heptylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-butylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-pentylcyclohexylmethoxy) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-hexylcyclohexylmethoxy) -cyclohexane r-l-cyano-l-heptyl-cis-4- (trans-4-heptylcycloheXylmethoxy) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-propylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-butylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-hexylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-propylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-butylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-pentylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-hexylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-butyl-cis-4- (trans-4-heptylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-butylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-hexylcyclohexoxymethyl) cyclohexane r-1-cyano-1-pentyl-cis-4- (trans-4-heptylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-propylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-butylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-pentylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-hexylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-hexyl-cis-4- (trans-4-heptylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-butylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-pentylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-hexylcyclohexoxymethyl) -cyclohexane r-1-cyano-1-heptyl-cis-4- (trans-4-heptylcyclohexoxymethyl) -cyclohexane r-1-cyano-1- (trans-4-propylcyclohexoxymethyl) -cis-4-propylcyclohexane r-l-cyano-l- (trans-4-butylcyclohexoxymethyl) -cis-4-propylcyclohexane r-l-cyano-1- (trans-4-pentylcyclohexoxymethyl) -cis-4-propylcyclohexane r-1 - cyano-1- (trans-4-hexylcyclohexoxymethyl) -cis-4-propylcyclohexane r-1-cyano-1- (trans-4-heptylcyclohexoxymethyl) -cis-4-propylcyclohexane r-1-cyano-1- (trans-4-propylcyclohexoxymethyl) -cis-4-butylcyclohexane r-1-Cyano-1- (trans-4-butylcyclohexoxymethyl) -cis-4-butylcyclohexane r-1-Cyano-1- (trans-4-pentylcyclohexoxymethyl ) -cis-4-butylcyclohexane r-1-cyano-1- (trans-4-hexylcyclohexoxymethyl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-4-heptylcyclohexoxymethyl) -cis-4-butylcyclohexane r-1-cyano-1- (trans-4-propylcyclohexoxymethyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (trans-4-butylcyclohexoxymethyl) -cis-4-pentylcyclohexane r-1-Cyano-1- (trans-4-pentylcyclohexoxymethyl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-4-hexylcyclohexoxymethyl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-4-heptylcyclohexoxymethyl) -cis-4-pentylcyclohexane r-1-cyano-1- (trans-4-propylcyclohexoxymethyl) -cis-4-hexylcyclohexane r-1-cyano-1- (trans-4-butylcyclohexoxymethyl) -cis-4-hexylcyclohexane r-l-cyano-l- (trans-4-pentylcyclohexoxymethyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (trans-4-hexylcyclohexoxymethyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (trans-4-heptylcyclohexoxymethyl) -cis-4-hexylcyclohexane r-1-Cyano-1- (trans-4-propylcyclohexoxymethyl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-4-butylcyclohexoxymethyl) -cis-4-heptylcyclohexane r-1-cyano-1- (trans-4-pentylcyclohexoxymethyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (trans-4-hexylcyclohexoxymethyl) -cis-4-heptylcyclohexane r-1-Cyano-1- (trans-4-heptylcyclohexoxymethyl) -cis-4-heptylcyclohexane.

Example 12 Analogously to Example 11, trans-1,4-dicyancyclohexane is obtained and 2 moles of 4-propyl-cyclohexyl bromide r-1-trans-4-dicyano-1,4-bis (trans-4-propylcyclohexyl) -cyclohexane.

The following is obtained analogously with the corresponding bromides: r-1-cyano-4-dicyano-1,4-bis- (trans-4-butylcyclohexyl) -cyclohexane r-1-trans-4-dicyan-1,4-bis- (trans-4-pentylcycloheXyl) -cyclohexane r-1-trans-4-dicyan-1, 4-bis- (trans-4-hexylcyclohexyl) -cyclohexane r-1-trans-4-dicyano-1,4-bis- (trans-4-heptylcyclohexyl) -cyclohexane r-1-trans-4-dicyano-1,4-bis (trans-4-methoxymethylcyclohexyl) cyclohexane.

Analogously with the corresponding 2-cyclohexylethyl or 2-phenylethyl bromides you get: r-1-trans-4-Dicyan-1,4-bis- [2- (trans-4-propylcyclohexyl) -ethyl] -cyclohexane r-1-trans-4-Dicyan-1,4-bis- [2- (trans-4-butylcyclohexyl) ethyl] cyclohexane r-1-Cyano-4-Dicyan-1,4-bis- [2- (trans-4-pentylcyclohexyl) -ethyl] -cyclohexane rl-trans-4-Dicyan-1,4-bis- [2- (trans -4-hexylcyclohexyl ) -ethylj -cyclohexane r-1-trans-4-dicyano-1,4-bis- [2- (trans-4-hexylcyclohexyl) ethyl] -cyclohexane r-1-trans-4-dicyano-1,4-bis-2-p-methoxyphenyl-ethyl) -cyclohexane r-1-trans-4-dicyano-1t4-bis-2-p-ethoxyphenyl-ethyl) -cyclohexane .

Example 13 A mixture of 24.3 g of r-1-cyano-1-p-hydroxyphenyl-cis-4-propyl-cyclohexane, 6.9 g of K2CO3, 25 g of hexyl iodide and 250 ml of DMF are heated to 80 ° for 16 hours while stirring, then cooled and worked up as usual. R-1-cyano-1-p-hexoxyphenyl-cis-4-propylcyclohexane is obtained.

Similarly, etherification gives: r-1-cyano-1-p-pentoxyphenyl-cis-4-propylcyclohexane r-1-cyano-1-p-heptoxyphenyl-cis-4-propylcyclohexane r-1-cyano-1-p-octoxyphenyl-cis-4-propylcyclohexane r-l-cyano-l-p-nonoxyphenyl-cis-4-propylcyclohexane r-1-cyano-l-p-decoxyphenyl-cis-4-propylcyclohexane.

Example 14 A mixture of 30.6 g of r-l-cyano-l-p-bromophenyl-cis-4-propylcyclohexane, 10 g Cu2 (CN) 2, 120 ml pyridine and 60 ml N-methylpyrrolidone are heated to 150 ° C. for 2 hours heated. It is cooled, a solution of 120 g FeCl3 6 H2O in 600 ml of 20% strength is added Hydrochloric acid added, heated to 70 ° for 1.5 hours while stirring, worked up as usual and receives r-1-cyano-1-p-cyanophenyl-cis-4-propylcyclohexane.

The following are examples of dielectrics according to the invention with a content on at least one compound of the formula I: Example A A mixture of 11% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane 24% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 21% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 21% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 13% r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane Shows 10% 4- (trans-4-pentylcyclohexyl) -4 '- (trans-4-propylcyclohexyl) -biphenyl F. -11 °, K. 75 Example B Dissolves in 98 parts by weight of the mixture according to Example A. 2 parts by weight of the blue dye 4,8-diamino-1,5-dihydroxy-2-p-methoxyphenyl-anthraquinone.

Degree of order of the dye 0.71.

Example C A mixture of 9% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 19% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 17% r-1-cyano-l-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 17% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 10% r-l-cyano-i-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane 28% 4-ethyl-2'-fluoro-4 '- (trans-4-pentylcyclohexyl) -biphenyl shows F. -16, K. 66 Example D In 98 parts by weight of the mixture according to Example C dissolves 2 parts by weight of the red dye l-p-dimethylaminobenzylidenamino-4-p-cyanophenylazonaphthalene. Degree of order of the dye 0.68.

Example E A mixture of 13% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane 27% r-l-cyano-l-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 23 % r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 23% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl ) -cyclohexane 14% r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane shows F. -9 °, K. 52 °.

Example F Dissolves in 99 parts by weight of the mixture according to Example E. 1 part by weight of perylene-3,9-bis-carboxylic acid bis (p-isopropylphenyl ester). Degree of order of the dye 0.73.

Example G A mixture of 12% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane 25% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 22% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cycl ohexane 22% r-l-cyano-l-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 13% r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane 6% trans, trans-4-propylcyclohexylcyclohexane-4'-carboxylic acid-trans- (4-propylcyclohexyl ester) shows F. -10, K. 59 °.

Example H A mixture of 12% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane 24% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 21% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 21% r-l-cyano-1-pentyl-cis-4- (trans-4-pentylcycloheXyl) -cyclohexane 13% r-l-cyano-l-propyl-cis-4- (trans-4-heptylcycloheXyl) -cyclohexane Shows 9% trans-4-pentylcyclohexanecarboxylic acid (p-trans-4-butylcyclohexylphenyl ester) M. -11 °, K. 63 Example I A mixture of 19% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 18% r-l-cyano-l-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 11% trans-4-propylcyclohexanecarboxylic acid (p-ethoxyphenyl ester) 9% 4- (trans-4-pentylcyclohexyl) -4 '- (trans-4-propylcyclohexyl) -biphenyl 28% 4-ethyl-2'-fluoro-4 '- (trans-4-pentylcyclohexyl) -biphenyl 15% trans-1- (p-ethoxyphenyl) -4-propylcyclohexane shows F. -15 °, K. 86 Example J A mixture of 18% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcycloheXyl) -cyclohexane 17% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 17% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 10% r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane 24% p- (trans-4-propylcyclohexyl) -benzoic acid- (4-butyl-2-cyanophenyl ester) 14% trans-1- (p-ethoxyphenyl) -4-propylcyclohexane shows m.p. -16, K. 63 °.

Example K A mixture of 19% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcycloheXyl) -cyclohexane 31% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 33% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 17% 4- (trans-4-pentylcyclohexyl) -4 '- (trans-4-propylcyclohexyl) -biphenyl is shown by F. -2 °, K. 91 °.

Example L A mixture of 11% r-1-cyano-1-pentyl-cis-4- (trans-4-propylcyclohexyl) cyclohexane 25% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 21% r-1-cyano-1-propyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 22% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 13% r-1-cyano-1-propyl-cis-4- (trans-4-heptylcyclohexyl) -cyclohexane 8% p- (trans-4-propylcyclohexyl) benzoic acid (trans -4-propylcyclohexyl ester) shows F. -11 °, K. 60 Example M A mixture of 22% r-1-cyano-1-heptyl-cis-4- (trans-4-propylcyclohexyl) -cyclohexane 20% r-l-cyano-l-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane 18% trans-4-pentylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) 10% 4- (trans-4-pentylcyclohexyl) -4 '- (trans-4-propyl cyclohexyl) -biphenyl 30% 4-ethyl-2'-fluoro-4' - (trans-4-pentylcyclohexyl) -biphenyl shows F. -12 °, K. 92 Example N A mixture of 17% r-1-cyano-1-pentyl-cis-4- (trans-4-pentylcycloheXyl) -cyclohexane 43% trans-4-propylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) 16% trans-4-pentylcyclohexanecarboxylic acid (trans-4-propylcyclohexyl ester) 17% p- (trans-4-propylcyclohexyl) benzoic acid (4-butyl-2-cyanophenyl ester) shows F. -16 °, K. 58

Claims (6)

Claims: ¼) Cyclohexane derivatives of the formula I R¹- (A¹) m-Z¹-A-Z²- (A²) n-R² I wherein R1 and R2 are each H, an alkyl group with 1 - 10 carbon atoms, which is also through one or two O atoms can be interrupted, F, C1, Br or CN, A1 and A2 respectively 1,4-phenylene, 1,4-cyclohexylene, unsubstituted or substituted by 1 - 4 carbon atoms 1,3-dioxane-2,5-diyl, piperldine-1,4-diyl, 1,4-bicyclo (2,2,2) octylene, or pyrimidine-2,5-diyl groups, A is a 1,4-cyclohexylene group substituted in the 1- and / or 4-position by F, C1, Br and / or CN, which can carry 1 or 2 further F, Cl or Br atoms and / or CN groups, Z1 and Z2 in each case -CO-O-, -O-CO-, -CH2CH2-, -OCH2-, -CH20- or a single bond, m is 1 or 2 and n is 0 or 1, with the two groups A1 being the same for m = 2 or can be different from one another, as well as the acid addition salts of the basic under these connections. 2. r-1-Cyano-1-pentyl-cis-4- (trans-4-pentylcyclohexyl) -cyclohexane. 3. Process for the preparation of cyclohexane derivatives of the formula I. according to claim 1, characterized in that one compound which otherwise has the formula I corresponds, but instead of H atoms one or more reducible groups and / or contains C-C bonds, treated with a reducing agent, or that to a compound which otherwise corresponds to formula 1, but instead of the remainder A contains a 1-cyclohexene-1,4-diyl group which has 1 or 2 additional F, Cl or Br atoms and / or may carry CN groups, a compound of the formula HX (in which X is F, C1, Br or CN denotes), or that for the preparation of esters of the formula I (in which z1 and / or z2 mean -CO-O- or -O-CO-) a corresponding carboxylic acid or one of their reactive derivatives with a corresponding alcohol or converts one of its reactive derivatives, or that one goes to Preparation of dioxane derivatives of the formula I (in which A1 and / or A2 are 1,3-dioxane-2,5-diyl mean) reacts a corresponding aldehyde with a corresponding diol, or that for the preparation of nitriles of the formula 1 (in which R1 and / or R2 are CN and / or in which A is substituted by at least one CN group) a corresponding one Carboxamide dehydrated or a corresponding carboxylic acid halide with Reacts sulfamide, or that for the preparation of nitriles of the formula I (in which A denotes a 1,4-cyclohexylene group substituted in the 1-position by CN) Acetonitrile of the formula II R¹- (A¹) m-Z1-CH2CN II in which R1, A11, Z1 and m are as indicated Have meanings with a compound of the formula III (X¹-CH2-CH2) 2CH-Z²- (A²) n-R² III where X1 is Cl, Br, I, OH or a reactive esterified OH group and R², A2, Z2 and n have the meanings given, or that for the preparation of nitriles of the formula I (in which A is in the 1- or 4-position 1,4-cyclohexylene group substituted by CN, which is additionally replaced by a or two F atoms and / or CN groups can be substituted; wherein further the one the radicals Z¹ or z2 denote a single bond) a nitrile of the formula IV Q1-A3CN IV wherein (a) R¹- (A¹) m-Z¹- or (b) R²- (A²) m-Z²- and A3 is an unsubstituted or a 1,4-cyclohexylene group which is mono- or disubstituted by F and / or'CN and R¹, R², A¹, A², Z1, Z², m and n have the meanings given with a compound of the formula V Q2-Xl V wherein Q² is (a) R²- (A²) n- or (b) R¹- (A¹) m and 1 1 2 1 2 X1, R1, R2, A1, A2, m and n have the meanings given, converts, or that for the preparation of ethers of the formula I (in which R1 and / or R2 one through one or two O atoms denote interrupted alkyl chain and / or Z1 and / or z2 a -OCH2- or -CH2O- group) etherifies a corresponding hydroxy compound, and / or that optionally a chlorine or bromine compound of the formula I (wherein R1 and / or R2 are Cl or Br and / or where A is replaced by at least one chlorine or bromine is substituted) with a cyanide, and / or that one optionally a base of the formula I by treatment with an acid in one of its acid addition salts converts, or that you optionally a compound of formula I from one of its Acid addition salts liberated by treatment with a base. 4. Use of the compounds of the formula I according to claim 1 as components liquid crystalline dielectrics for electro-optical display elements. 5. Liquid-crystalline dielectric for electro-optical display elements with at least two liquid-crystalline components, characterized in that at least one component is a compound of the formula I according to claim 1. 6. Electro-optical display element, characterized in that it a dielectric according to claim 4 contains.