Anodic addition of hydroxy and benzoyloxy groups to stilbenes

Abstract
The anodic reaction of benzoic acid in acetonitrile has been carried out in the presence of trans- and cis-stilbenes using platinum electrodes. The reaction with added trans-stilbene gave meso-hydrobenzoin dibenzoate together with threo-2-benzoyloxy-1,2-diphenylethanol. Under similar conditions, cis-stilbene also gave these products. No evidence for the isomerization of cis-stilbene to the trans-isomer during the electrolysis was found. Stereoisomeric dl-hydrobenzoin dibenzoate and erythro-2-benzoyloxy-1,2-diphenylethanol were not obtained from either stilbene. For comparison, the "wet" Prévost reaction of cis-stilbene with silver acetate and iodine was studied. These results are discussed on the basis of a stepwise oxidation mechanism which involves a cyclic 1,2-benzoxonium ion intermediate.