| abstract |
Novel compounds of the formula wherein Z 1 and Z 2 are each H, alkyl, aralkyl, aryl, alkenyl or alkynyl not conjugated with the ring, cycloalkyl, cycloalkenyl or heterocyclic, or Z 1 + Z 2 is alkylene R is OH, Cl or OR1 in which R1 is C 1-6 alkyl, 5-benzyl-fur-3-ylmethyl, dicarboximidomethyl, heterocyclic or 2-methyl- 3-R11-6-keto-cyclopent-2-enyl wherein R11 is alkyl, alkenyl, alkynyl, aryl, aralkyl, cycloalkyl, cycloalkenyl or heterocyclic A is in which R 1 is H or alkyl, R 2 and R 3 are each alkyl, aralkyl, aryl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, or heterocyclic, R 3 having at least 2 carbon atoms, or R 2 and R 3 and the adjacent C atom form a C 3-7 carbon homocycle, saturated or unsaturated and optionally mono- or di-methyl or ethyl and/or methoxy or ethoxy substituted, or a polynuclear aromatic system or a similarly optionally substituted heterocycle, R 4 is methyl or ethyl, R 5 is H, methyl or ethyl or R 4 and R 5 form a saturated or unsaturated fused on homocycle or heterocycle, and Y and Y1 are aliphatic hydrocarbon chains, are prepared by reacting a sulphone of the formula H-A-SO 2 -Ar (Ar is optionally substituted aryl) in the presence of a basic agent with a compound of the formula Z 1 . Z 2 .C = CH.CO 2 R1 (R1 is C 1-6 -alkyl) to give products where R1 is C 1-6 alkyl which may be then transesterified or hydrolysed to the free acids and these re-esterified via functional derivatives such as the acid halides. The racemic acids may be resolved by means of an optically active organic base. The novel compounds wherein R 1 is H, Z 1 and Z 2 are each CH 3 and R 2 and R 3 and the intervening carbon atom form a 3 or 4 carbon homocycle are also prepared by reacting a cyclopropyl or cyclobutyl triaryl phosphonium halide with dl-trans-caronaldehydic acid. Other novel compounds comprise the l-ephedrine salts of d- and l-trans-3,3-dimethyl-2- cyclopentylidenemethyl - 1 - cyclopropane carboxylic acid, the d- and l-forms of this acid and the d- and dl-forms of the sodium salt of this acid. Reference has been directed by the Comptroller to Specification 1,168,797. |