Electrochemical oxidation of allenic hydrocarbons in acetonitrile

Abstract

The anodic oxidation of a variety of alkyl-substituted allenes, terminal and internal ones, has been investigated in acetonitrile. All compounds studied were found to undergo 2e^– oxidation followed by nucleophilic attack by acetonitrile and water molecules, to form products containing at least two of the following functicnal groups, CC, NHCOCH₃, CO, and OH. The effect of various parameters (concentration, electrolyte, oxidation potential, temperature, and anode material) on the electro-oxidation of a model compound (nona-1,2-diene) has been studied and a general mechanistic scheme is presented and discussed.