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The synthesis of the 1and 1,1'-phenylethenylferrocenes of controlled stereochemistry exhibiting π-extended conjugation was satisfactorily carried out by reaction of 1,1'-ferrocene dicarboxaldehyde with p-(X-benzyl)(triphenyl)phosphorane (X= NO2, NMe2). Moreover, the Wittig reaction of (E)or (Z)-1'-p-(X-phenyl)ethenyl-1-ferrocenecarboxaldehyde shows a template effect produced by the phenylethenyl chain, which was analysed. Cyclic voltammetry studies of 1and 1,1'-p-(X-phenyl)ethenylferrocenes exhibit shifts in oxidation potentials which are consistent with the more effective conjugation of the E than Z isomers, and the electron acceptor character of NO2 vs. NMe2 or CHO vs. H. Keyword: Wittig reaction, vinylferrocene, template effect, isomerization, cyclic voltammetry

Stereo chain template effect on the synthesis of conjugated 1,1´-di-[p-(X-phenyl)ethenyl]ferrocenes