Pummerer rearrangement
From Biocrawler, the free encyclopedia.
The Pummerer rearrangement is a chemical reaction whereby an alkyl sulfoxide rearranges to an α-acyloxythioether in the presence of acetic anhydride.
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Mechanism
The mechanism of the Pummerer rearrangement begins with the acylation of the sulfoxide (1 and 2). Compound 3 undergoes elimation to produce the sulfonium ion 4. Acetate adds to the sulfonium ion to give the final product 5.
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References
- Pummerer, R.; Ber. 1910, 43, 1401.
