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Pummerer Rearrangement
The Pummerer rearrangement is a well-established rearrangement of a sulfoxide to an α–acyloxy–thioether, which has an array of useful synthetic implications. In the presence of an anhydride like acetic anhydride, the sulfoxide-O is acylated, which is rapidly eliminated to generate a thial intermediate 1. 1 is typically acylated to generate the desired α–acyloxy–thioether product; however, the thial can be interrupted by a wide array of nucleophiles and therefore has noted applications in total synthesis.
- Reagents:
- Acetic anhydride, Trifluoroacetic anhydride, Triflic anhydride, Trimethylsilyl trifluoromethanesulfonate
- Reactants:
- Sulfoxides
- Products:
- α–Acyloxy–thioethers
- Scheme:
-
- Original literature:
-
- Über Phenyl-sulfoxyessigsäure
- Über Phenylsulfoxy-essigsäure. (II.)
- Review literature:
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- Recent advances in Pummerer Reactions
