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Electrocatalytic Oxidative Cleavage of Electron-Deficient Substituted Stilbenes in Acetonitrile-Water Employing a New High Oxidation Potential Electrocatalyst. An Electrochemical Equivalent of Ozonolysis

Xin Wu, Anthony P. Davis and Albert J. Fry*

*Chemistry Department, Wesleyan University, Middletown, Connecticut 06459, Email: afrywesleyan.edu

X. Wu, A. P. Davis, A. J. Fry, Org. Lett., 2007, 9, 5633-5636.

DOI: 10.1021/ol7026416 (free Supporting Information)


Abstract

A series of symmetrical and unsymmetrical stilbenes bearing electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation employing a high oxidation potential triphenylamine electrocatalyst. The oxidations apparently involve the corresponding 1,2-diols, which are also converted to aldehydes in high yield under the same conditions.

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Key Words

Aldehydes, Electrochemistry


ID: J54-Y2007-4200