Disubstituted cyclohexane or tetrahydropyran derivative preparation, for use e.g. in liquid crystals, by trans-selective hydrogenation of cyclohexene or dihydropyran derivative over transition metal phosphine complex

摘要

Production of 1,4-disubstituted cyclohexane or 2,5-disubstituted tetrahydropyran derivatives (I) involves hydrogenating a corresponding cyclohexene or dihydropyran derivative (II) in presence of a transition metal complex (III) stabilized by one or more same or different phosphine ligands. Production of cyclohexane or tetrahydropyran derivatives (I) of formula (IA) or (IB) involves hydrogenating a corresponding cyclohexene or dihydropyran derivative (II) of formula (IIA) or (IIB) in presence of a transition metal complex (III) stabilized by one or more same or different phosphine ligands. [Image] [Image] W : O or CH 2; a - e and f - j : 0 or 1, provided that e and j = 1 if W = CH 2; A 1>1>- A 1>5>, A 2>1>- A 2>5>1,4-cyclohexylene (in which 1 or 2 non-adjacent CH 2groups are optionally replaced by O and/or S), 1,4-phenylene (in which 1 or 2 non-adjacent CH groups are optionally replaced by N), naphthalene-2,6-diyl or 1,2,3,4-tetrahydronaphthalene-2,6-diyl (all optionally substituted (os) by one or more of halo or CN); or 1,3-cyclobutylene, piperidine-1,4-diyl or decahydronaphthalene-2,6-diyl; R 1>1>H or 1-15C alkyl (os and optionally having one or more CH 2groups replaced by CC, S, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked), provided that R 1>1>is not H if a = b = 0 and Z 1>2>= direct bond; R 2>1>H or 1-15C alkyl (os and optionally having one or more CH 2groups replaced by CH=CH, CC, S, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked), provided that R 2>1>is not H if f = g = 0 and Z 2>2>= direct bond; Y 1>1>H, halo, NCS, SCN, SF 6or CN; or 1-15C alkyl (os by one or more of halo or CN) or 7-16C aralkyl (os by one or more of halo, NO 2, alkanoyl, alkoxy, NH 2or dialkanoylamino) (both optionally having one or more CH 2groups replaced by CC, S, SO, SO 2, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked); Y 2>1>H, halo, NCS, SCN, SF 6or CN; or os 1-15C alkyl or 7-16C aralkyl (both optionally having one or more CH 2groups replaced by CH=CH, CC, S, SO, SO 2, O, CO, COO, OCO or OCOO, provided that heteroatoms are not directly linked); Z 1>1>, Z 1>3>- Z 1>5>direct bond, CH 2CH 2, CF 2CF 2, CHCF 2, CF 2CH 2, CHFCHF, CC, CH 2O, OCH 2, CF 2O, OCF 2, COO or OCO; Z 2>1>, Z 2>3>- Z 2>5>direct bond, CH=CH, CH 2CH 2, CF 2CF 2, CHCF 2, CF 2CH 2, CHFCHF, CC, CH 2O, OCH 2, CF 2O, OCF 2, COO or OCO; Z 1>2>direct bond, CH 2CH 2, CC, CH 2O, OCH 2, COO or OCO; Z 2>2>direct bond, CH=CH, CH 2CH 2, CC, CH 2O, OCH 2, COO or OCO. An independent claim is included for compositions comprising a compound (II) and at least one of the stabilized complexes (III).