Liquid crystalline or mesogenic naphthalene derivative preparation, by reacting side-chain component with naphthalene endo-oxide derivative followed by dehydration or hydrogenation

摘要

Preparation of liquid crystalline or mesogenic naphthalene derivatives (I) involves: (a) nucleophilic addition of a compound containing a side-chain group (IV) with a naphthalene endo-oxide derivative (III), optionally in presence of a transition metal catalyst; and (b) converting the product (II) into (I) by dehydration if (II) contains a hydroxy-substituted naphthalene group or by hydrogenation if (II) contains a naphthalene endo-oxide group. Compounds (I), (II) and (III) are new. Preparation of liquid crystalline or mesogenic naphthalene derivatives of formula R1-(A1-Z1)m1-(A2-Z2)m2-W-(Z3-A3)m3-(Z4-A4)m4-R2 (I) involves: (a) nucleophilic addition of a compound containing a group of formula R1-(A1-Z1)m1-(A2-Z2)m2- (IV) with a naphthalene endo-oxide derivative of formula (III), optionally in presence of a transition metal catalyst; and (b) converting the product of formula R1-(A1-Z1)m1-(A2-Z2)m2-W-(Z3-A3)m3-(Z4-A4)m4-R2 (II) into (I) by dehydration if Q is a hydroxy-substituted naphthalene derivative group or by hydrogenation if Q is naphthalene endo-oxide derivative group. W = 1-(L1)-3-(L2)-4-(L3)-naphthalene-2,6-diyl, 1-(L1)-3-(L2)-4-(L3)-naphthalene-2,7-diyl, 1-(L1)-3-(L2)-4-(L3)-5,6,7,8-tetrahydro-naphthalene-2,6-diyl or 1-(L1)-3-(L2)-4-(L3)-5,6,7,8-tetrahydro-naphthalene-2,7-diyl; L1 - L3 = H or F; R1, R2 = H, halo, CN, NCS, SF5, 1-18C alkyl (optionally having one or two (non-adjacent) CH2 groups replaced by O, S, CO, OCO, COO, CH=CH, CF=CF and/or CC; optionally having one or more CH groups replaced by N; and optionally substituted by one or more halo and/or CN), diallylamino, dibenzylamino or benzyloxy; A1 - A4 = 1,4-cyclohexenylene or 1,4-cyclohexylene (both optionally having one or two (non-adjacent) CH2 groups replaced by O or S), 1,4-phenylene (optionally having one or two CH groups replaced by N), piperidine-1,4-diyl, 1,4-bicyclo (2.2.2) octylene, phenanthrene-2,6-diyl, naphthalene-2,6-diyl, decahydronaphthalene-2,6-diyl, 1,2,3,4-tetrahydronaphthalene-2,6-diyl, 1,3-bicyclobutylene, 1,3-bicyclo (1,1,1) pentylene or spiro-(3,3)-heptane-3,6-diyl (all optionally substituted by one or more halo); Z1 - Z4 = COO, OCO, CF2O, OCF2, CH2O, OCH2, CH2CH2, (CH2)4, CH2CHMe, CH=CMe, C2F4, CH2CF2, CF2CH2, CF=CF, CF=CH, CH=CF, CH=CH, CC or a combination of two of these groups (provided that two O atoms are not directly bonded to each other); m1 - m4 = 0-2; Q = 1-(L1)-3-(L2)-4-(L3)-5-hydroxy-5,6-dihydronaphthalene-2,6-diyl, 1-(L1)-3-(L2)-4-(L3)-8-hydroxy-7,8-dihydronaphthalene-2,7-diyl or a naphthalene-endo-oxide derivative group of formula (a) or (b). Independent claims are included for the products (I) and the intermediates (III) and (II) as new compounds.