Cyanomethylation versus reductive saturation and hydrodimerisation during the electroreduction of αβ-unsaturated nitriles in acetonitrile

Abstract

Results for the electroduction of cinnamonitrile, 3-methylcinnamonitrile, and acrylonitrile in acetonitrile under a variety of conditions are reported in detail, and the factors which favour the formation of glutaronitrile derivatives (cyanomethylation)versus reductive saturation and hydrodimerisation have been identified. Cyanomethylation of acrylonitrile has also been studied using (i) azobenzene–acetonitrile, and (ii) phenylsulphonylacetonitrile–dimethylformamide, as the source of electrogenerated -CH₂CN.