The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an α-acyloxy–thioether in the presence of acetic anhydride. In this reaction, sulfur is reduced while adjacent carbon is oxidized.
Several reviews have been published.
The usage of α-acyl sulfoxides and Lewis acids, such as TiCl4 and SnCl4, allow the reaction to proceed at lower temperatures (0 °C).
Common activators besides acetic anhydride are trifluoroacetic anhydride and trifluoromethanesulfonic anhydride. Common nucleophiles besides acetates are arenes, alkenes, amides, and phenols.
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