Mechanism of Anodic Cleavage of Benzyl Ethers

Article abstract of DOI:10.1021/ja00531a030

Kinetic isotope effects and substituent effects are utilized to elucidate the mechanism of the anodic oxidation of benzyl ethers at platinum in acetonitrile.All of the data, including some previously published results, are consistent with a mechanism involving phenylalkoxy carbonium ions.Much of the data is incompatible with a previous mechanistic proposal involving initial oxidative cleavage of the benzyl carbon-oxygen bond.