Electrochemical oxidation of allenic hydrocarbons in acetonitrile

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, C[double bond, length half m-dash]C, NHCOCH3, C[double bond, length half m-dash]O, 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.