Process for the preparation of alkenylbenzenecarboxylic acid derivatives and alkenylnaphthalenecarboxylic acid derivatives

DETAILED DESCRIPTION What is claimed is: 1.
A process for the preparation of a compound of the formula I ##STR61## in which m is zero or 1, p is 1 or 2, Z is substituted or unsubstituted phenyl or naphthyl if p=1, and substituted or unsubstituted phenylene or naphthylene if p=2, R is hydrogen, C.
sub.
1-4 -alkyl, --CH.
sub.
2 COOR" or --CH.
sub.
2 CH.
sub.
2 CN and R' is hydrogen, or, if p=1 and m=zero, can also be C.
sub.
1-4 -alkyl, --CN or --COOR", but at least one of R and R' must by hydrogen, Y is --CN, --COOR", --CON(R").
sub.
2 or --COR" and the radicals R", independently of one another, are C.
sub.
1 -C.
sub.
12 -alkyl or phenyl, which comprises reacting a compound of the formula II ##STR62## in which Z, m and p are as defined for formula I and X is chlorine, bromine or iodine, with a compound of the formula III or if desired, where p=2, with a mixture of two different compounds of the formula III ##STR63## in which R, R' and Y are as defined for formula I, in the presence of a base and with the addition, as a catalyst, of palladium metal or of a palladium compound which under the reaction conditions forms a phosphorus-free labile palladium(O) compound.
2.
A process according to claim 1, wherein a compound of the formula II, in which X is clorine, is used.
3.
A process according to claim 1, wherein the palladium compound used in PdCl.
sub.
2, PdBr.
sub.
2, Pd(OOCCH.
sub.
3).
sub.
2, ##STR64## Pd(OOCCH.
sub.
3).
sub.
2 (2,2'-bipyridyl), PdCl.
sub.
2 (NC-phenyl).
sub.
2, bis-(dibenzylidene-acetone)-palladium(O) or bis-(cyclohexylisonitrile)-palladium(O).
4.
A process according to claim 1, wherein the palladium compound used is PdCl.
sub.
2, palladium acetate or bis-(dibenzylidene-acetone)-palladium(O).
5.
A process according to claim 1, wherein the reaction is carried out at a temperature of between 0.
degree.
and 200.
degree.
C.
and in the presence of an organic solvent which is inert towards the reactants.
6.
A process according to claim 5, wherein the solvent used is anisole, a xylene, or toluene.
7.
A process according to claim 1, wherein the base used is a compound of the formula VI ##STR65## in which Q