Anodic oxidation of stilbenes bearing electron-withdrawing ring substituents

Abstract

A number of disubstituted stilbenes bearing either two strong electron-withdrawing groups or one electron-withdrawing and one electron-donating group were synthesized and anodically oxidized in a divided cell in methanol at a carbon anode. A variety of types of products were obtained, most of which have never been observed upon oxidation of alkenes not bearing electron-withdrawing groups. A mechanistic scheme involving 2-methoxy-1,2-diarylethyl cations as key intermediates can account for all of the observed products. The nature of the products from each alkene is strongly correlated with the sum of the Hammett σ + values of the ring substituents.