Patent DE-102005022716-A1 (DE)
Title: Preparation of carbocyclic compounds with five or six benzocondensed rings, useful in liquid crystalline medium, comprises subjecting phenyl derivative to ring closing metathesis reaction in the presence of metathesis catalyst
Inventor: POETSCH EIKE
IPC: C07C255/50
Filed: 2005-05-18
Abstract: Preparation of carbocyclic compounds with 5-6 benzocondensed rings, comprises subjecting a phenyl derivative (arranged with two substitutents in ortho position to each other) to ring closing metathesis reaction in the presence of at least one metathesis catalyst. Preparation of carbocyclic compounds with 5-6 benzocondensed ring compounds, comprises subjecting a phenyl derivative (arranged with two substitutents in ortho position to each other, that respectively have an aliphatic C-C-double bond and together in the case of the five benzocondensed ring compounds have at least 5 carbon atoms and in the case of six benzocondensed ring compounds have at least 6 carbon atoms ) to ring closing metathesis reaction in the presence of at least a metathesis catalyst. Independent claims are also included for: (1) benzocondensed ring compounds of formula (II)-(VI); (2) five or six benzocondensed ring compound of formula (I); (3) composition of (I) comprising (Ia) and (Ib); (4) composition of (I) comprising (Ie) and (Id) or (If); and (5) liquid crystalline medium comprising at least (I). W1>-substituted cyclic ring : 5-6 membered cyclic ring selected from (i)-(vii); MG1>R1>-[A2>-Z2>-]b-[A3>-Z3>-]c; a, b, c : 0-1; L1>, L2>T or H (any one of L2> is T); T : F, Cl, CN, unsubstituted or substituted with CN, halo substituted 1-15C alkyl residue (in which one or more CH2-groups may be replaced with -Ctriple boundC-, -CH=CH-, -O-, -S-, -SO2-, -C(O)-, -C(O)-O- or -O-C(O)-, where the heteroatoms in the alkyl residue chain are not connected directly together); X1>H, halo, CN, NCS, SF5, unsubstituted or substituted with CN, halo substituted 1-15C alkyl residue (in which one or more CH2-groups may be replaced with -Ctriple boundC-, -CH=CH-, -O-, -S-, -SO2-, -C(O)-, -C(O)-O- or -O-C(O)-, where the heteroatoms in the alkyl residue chain are not connected directly together); A1>-A3>1,3-cyclobutanyl-, 2,6-spiro[3.3]heptanyl, 1,4-cyclohexanyl, 2,5-[1,3]dioxanyl, 2,5-tetrahydro-pyranyl, 1,4-benzenyl-substituted with (F)d, 2,6-tetrahydro-naphthalenyl-substituted with (F)e or 2,6-naphthalenyl-substituted with (F)f and (F)e; d : 0-4; e, f : 0-3; R1>H, CN, unsubstituted or substituted with CN or OH, halo substituted 1-15C alkyl residue (in which one or more CH2-groups are replaced through -Ctriple boundC-, -CH=CH-, -O-, -S-, -SO2-, -C(O)-, -C(O)-O- or -O-C(O)-, where the heteroatoms in the alkyl residue chain are not connected directly together); Z1>single bond, CH2CH2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH2O-, -OCH2-, -CF2O-, -OCF2-, -C(O)-O-, -O-C(O)-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- or -Ctriple boundC-; and Z2>, Z3>single bond, -CH2CH2-, -CF2CH2-, -CH2CF2-, -CF2CF2-, -CH2O-, -OCH2-, -C(O)-O-, -O-C(O)-, -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- or -Ctriple boundC-. In formula (I), when W1>-substituted cyclic ring is (iii) or (vii), then Z1>-Z3> is not -CH=CH-, -CF=CH-, -CH=CF-, -CF=CF- or -Ctriple boundC- and R1>, L1>, L2> and X1> do not represent -CH=CH- or -Ctriple boundC-unit in the alkyl residue; when W1>-substituted cyclic ring is (ii) or (iii), a is 0, b and/or c is 1, then L1> is F or Cl; and X1> is not -CN, -NCS, -SF5 or alkyl residue replaced with CN. [Image] [Image] [Image] [Image] [Image] [Image] [Image] [Image].