The Journal of Organic Chemistry

Quinone dehydrogenation. Oxidation of benzylic alcohols with 2, 3-dichloro-5, 6-dicyanobenzoquinone

HD Becker, A Bjoerk, E Adler

Index: Becker, Hans-Dieter; Bjoerk, Anders; Adler, Erich Journal of Organic Chemistry, 1980 , vol. 45, # 9 p. 1596 - 1600

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Citation Number: 113

Abstract

2, 3-Dichloro-5, 6-dicyanobenzoquinone (DDQ) reacts with primary and secondary aryl- substituted alcohols under mild conditions in dioxane solution to give the corresponding carbonyl compounds in high yields. In contrast to other oxidants, DDQ can be applied advantageously for the oxidation of hydroxyaryl-substituted alcohols. A mechanism involving participation of the phenolic hydroxyl group in the dehydrogenation reaction is discussed. ...