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Letter

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

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

Chemistry Department, Wesleyan University, Middletown, Connecticut 06459

Org. Lett., 2007, 9 (26), pp 5633–5636

DOI: 10.1021/ol7026416

Publication Date (Web): November 30, 2007

Abstract

A series of symmetrical and unsymmetrical stilbenes bearing two or more strong electron-withdrawing groups were oxidatively cleaved to the corresponding aldehydes in high yield by electrocatalytic anodic oxidation in aqueous acetonitrile employing a new 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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History

Published In Issue December 20, 2007
Received October 31, 2007

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Letter

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

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Enantioselective Intramolecular Friedel−Crafts-Type α-Arylation of Aldehydes

A General Method for the Synthesis of Nonracemic trans-Epoxides: Concise Syntheses of trans-Epoxide-Containing Insect Sex Pheromones

Indium−Copper-Mediated Barbier−Grignard-Type Alkylation Reaction of Imines in Aqueous Media

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