Reduction of Vicinal Dihalides. I. The Electrochemical Reduction of meso and (±)-1,2-Dibromo-1,2-diphenylethane

Abstract

The mechanism of the electrochemical dehalogenation of organic vicinal dihalides has been examined in acetonitrile by using meso- and (±)-1,2-dibromo-1,2-diphenylethane. Reduction potentials and product distributions obtained from the isomeric dibromides could not be accommodated within a mechanism involving a concerted addition of two electrons. However, these results can be explained by a stepwise addition of electrons, allowing the possibility of bond rotation at an intermediate stage. The product distributions obtained from the reduction of the (±)- dibromide were found to be potential-dependent, a result not previously observed for this compound, but consistent with a stepwise mechanism.