Co-oxidation of ferrocene and hydrazine derivatives. Formation of substituted ferrocenes

Abstract

Oxidation of a mixture of ferrocene and phenylhydrazine with silver oxide in acetic acid affords phenylferrocene and 1,l'-diphenylferrocene. The reaction may also be conducted in acetone or benzene solvent, and benzoquinone may be used as the oxidizing agent. Similar transformations have been observed using p-methoxyphenyl-, p-chlorophenyl-, p-nitrophenyl-, 2,4-dinitrophenyl-, α-naphthyl-, benzyl-, methyl-, and benzoyl-hydrazine, but the reaction failed with acetylhydrazine. The mechanism of the reaction appears to involve free-radical substitution of ferricinium ion.