Electro-organic reactions. Part 10. Mechanism of anodic cleavage of dibenzyl ether

Abstract

A detailed study of the voltammetry, coulometry, and products of the anodic oxidation in acetonitrile of dibenzyl ether suggests that, contrary to earlier reports, a one-electron oxidation occurs with the first-formed radical cation undergoing irreversible fragmentation. The subsequent chemical reactions are complex but a mechanistic scheme is presented which is consistent with the above and with additional experiments including an examination of the products of oxidation of dibenzyl [¹⁸O]ether.