Ciba-geigy Corporation

Alwyn Spencer

Dieter Reinehr

Hans-Ulrich Blaser

Kurt Weber

Daniel Bellus

Guglielmo Kabas

Novel compounds of the formula ##STR1## and processes for their preparation are described. X represents bromine or iodine and R.sub.1, R.sub.2 and R.sub.3 have the meaning indicated in the patent claim. The compounds (I) are valuable intermediates for the preparation of fluorescent brighteners of the divinylstilbene type.

4-halogenostilbene derivatives and processes for their preparation

Stilbene-4,4'-dialdehyde can be produced by reaction of ethylene with 4-bromobenzaldehyde in the presence of a base and of a palladium compound as catalyst in a simple and economical manner in high yields, by performing the reaction under a partial pressure of ethylene of 0.01 to 1 bar. The stilbene-4,4'-dialdehyde obtained is suitable for example for producing optical brighteners.

Process for producing stilbene-4,4'-dialdehyde

Compounds of the formula I ##STR1## in which A is C.sub.2-12 -alkenyl, C.sub.4-8 -cycloalkenyl or a grouping--C(R).dbd.C(R')--Y and Y, R, R', R.sub.1, R.sub.2, R.sub.3 and R.sub.3 ' are as defined in patent claim 1, can be prepared in high yields in a simple and economical manner by reacting corresponding bromobenzenes or iodobenzenes with a compound HA in the presence of an alkali metal salt or alkaline earth metal salt of an aliphatic monocarboxylic acid having 1-12 C atoms or benzoic acid, of a cyclic or N,N-disubstituted amide as the solvent, particularly N,N-dimethylformamide, and of a palladium compound which can, if desired, contain arsenic or phosphorus, as the catalyst.

Process for the Pd-catalyzed arylation of olefins with aryl halides

Process for the preparation of styrene derivatives and/or stilbene

The invention relates to vinylstilbene compounds of the formula ##STR1## wherein Q is the grouping --COX or ##STR2## These compounds are obtained by reacting 1 molar equivalent of a compound of the formula II ##STR3## wherein X is chlorine, bromine or iodine, in the presence of a base and with the addition of palladium metal or of palladium compounds, as catalyst, which, under the reaction conditions, form labile palladium(O) compounds which do not contain phosphorus, with 1 molar equivalent of a compound of the formula III or with 1 molar equivalent of each of the compounds of the formulae III and IV ##STR4##

Process for the production of vinylstilbene compounds

Compounds of the formula I ##STR1## in which Z, Z.sub.1, R, m and p are as defined in patent claim 1, can be obtained in a simple and economical manner by a novel process wherein a halide of the formula II ##STR2## is reacted with a substituted or unsubstituted vinylbenzene or vinylnaphthalene derivative in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I) or functional derivatives preparable therefrom are useful, for example, for the preparation of known dyes or fluorescent brighteners, or can be used directly as fluorescent brighteners or as scintillators.

Process for the preparation of alkenylbenzene derivatives or

Compounds of the formula I ##STR1## in which p, m, Z, R, R' and Y are as defined in claim 1, can be obtained in a simple and economical manner by a novel process which comprises reacting a halide of the formula ##STR2## with the corresponding acrylic acid derivative, in the presence of a base and of certain palladium catalysts, such as palladium acetate. The compounds (I), and functional derivatives prepared therefrom, are useful for the preparation of photocrosslinkable polymers, which can in particular be employed as (so-called) photoresists.

Growing community of inventors

Basel, Switzerland

Alwyn Spencer