| Pummerer rearrangement | |
|---|---|
| Named after | Rudolph Pummerer |
| Reaction type | Rearrangement reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000220 |
The Pummerer rearrangement is an organic reaction whereby an alkyl sulfoxide rearranges to an α-acyloxy–thioether (monothioacetal-ester) in the presence of acetic anhydride.[1][2][3]
The stoichiometry of the reaction is:
- RS(O)CHR'2 + Ac2O → RSC(OAc)R'2 + AcOH
- ^ de Lucchi, Ottorino; Miotti, Umberto; Modena, Giorgio (1991). The Pummerer Reaction of Sulfinyl Compounds. Vol. 40. pp. 157–184. doi:10.1002/0471264180.or040.03. ISBN 978-0471264187.
{{cite book}}:|journal=ignored (help) - ^ Padwa, Albert; Gunn, David E. Jr.; Osterhout, Martin H. (1997). "Application of the Pummerer Reaction Toward the Synthesis of Complex Carbocycles and Heterocycles". Synthesis. 1997 (12): 1353–1377. doi:10.1055/s-1997-1384.
- ^ Padwa, Albert; Bur, Scott K.; Danca, Diana M.; Ginn, John D.; Lynch, Stephen M. (2002). "Linked Pummerer-Mannich Ion Cyclizations for Heterocyclic Chemistry". Synlett. 2002 (6): 851–862. doi:10.1055/s-2002-31891.