Journal of Organic Chemistry p. 4851 - 4855 (1987)
Update date:2022-08-15
Topics:
Amon, Catherine M.
Banwell, Martin G.
Gravatt, G.Lance
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.
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