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Compounds with the structure ArCH2X (X = OH, OR, and OCOlv) were oxidized at a platinum electrode in acetonitrile. The major products of controlled potential electrolysis were ArCHO and XH. The mechanism of benzyl ether cleavage was studied. A scheme involving initial electron loss from the aromatic moiety, formation of an alkoxyphenyl carbonium ion, and cleavage of RO via a hemiacetal is indicated. This study arose from a desire to reconcile demonstrations that certain materials were electrooxidatively cleaved with reports that these same materials were major products in similar electrolyses. Recent studies have demonstrated the feasibility of anodic side chain substitution reactions. These reactions convert hydrocarbons to benzylic alcohols, acetamides, ethers, or esters. The one mechanistic facet that has been established in most of these reactions is that the oxidation is initiated by removal of electron(s) from the aromatic 7 system.

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