Oxidation of Vicinal Diols to α-Dicarbonyl Compounds by Trifluoroacetic Anhydride "Activated" Dimethyl Sulfoxide

Article abstract of DOI:10.1021/jo00231a005

Trifluoroacetic anhydride "activated" dimethyl sulfoxide is an effective oxidant for the conversion of vicinal diols into the corresponding α-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 ?-homo-o-benzoquinone, and a "hyperreactive" α-keto aldehyde.