Electrochemical Reductive Carboxylation: Reduction of Unsaturated Compounds in the Presence of Methyl Chloroformate

Article abstract of DOI:10.1021/jo00165a013

Mono- and dicarboxylated derivatives have been obtained by electroreduction of various unsaturated compounds in acetonitrile at a mercury-pool cathode in the presence of methyl chloroformate.Unsaturated compounds included activated olefins, ketones, aromatic Schiff bases, nitro compounds, and nitrogen heterocycles.The distribution of the products and their yields depend on the nature of the supporting electrolyte (Et4NClO4 or LiClO4).Reduction mechanisms accounting for the nature of the reduction products are proposed on the basis of voltammetric and coulometric data.In some cases it is possible to obtain the kinetic parameters.