Oxidation of vicinal diols to. alpha.-dicarbonyl compounds by trifluoroacetic anhydride-activated dimethyl sulfoxide

CM Amon, MG Banwell, GL Gravatt

Index: Amon, Catherine M.; Banwell, Martin G.; Gravatt, G.Lance Journal of Organic Chemistry, 1987 , vol. 52, # 22 p. 4851 - 4855

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Citation Number: 70

Abstract

Trifluoroacetic anhydride" activated" dimethyl sulfoxide is an effective oxidant for the conversion of vicinal diols into the corresponding a-dicarbonyl compounds or products derived therefrom. Unlike the Swern oxidant, the title reagent system gives good yields of products derived from halogenated substrates. The method has permitted syntheses of previously inaccessible compounds including tropolones, a u-homo-o-benzoquinone, and ...