Mechanism of anodic cleavage of benzyl ethers

JW Boyd, PW Schmalzl, LL Miller

Index: Boyd, Jean W.; Schmalzl, Paul W.; Miller, Larry L. Journal of the American Chemical Society, 1980 , vol. 102, # 11 p. 3856 - 3862

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Citation Number: 29

Abstract

Abstract: 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 benzylic carbon-oxygen bond.