Electrochemical Syntheses. IV. The Homolytic Methoxylation and Ethoxylation of Olefins by the Anodic Oxidation of Methanol and Ethanol

The electrochemical oxidation of methanol and ethanol in the presence of trans-stilbene, cis-stilbene, norbornene, and styrene has been studied. The major gaseous and nongaseous products have been identified and determined, and the corresponding dimethoxylated derivatives and diethoxylated derivatives have been obtained in fairly high yields. The main path by which these products may have arisen has been discussed, and the stereochemistry of the addition of methoxy radicals to stilbene has been discussed. Particular attention has been given to the possibility that the main product arises from the anodic oxidation of an intermediate radical to a carbonium ion.