The Pfitzner–Moffatt oxidation, sometimes referred to as simply the Moffatt oxidation, is a chemical reaction which describes the oxidation of primary and secondary alcohols by dimethyl sulfoxide (DMSO) activated with a carbodiimide, such as dicyclohexylcarbodiimide (DCC). The resulting alkoxysulfonium ylide rearranges to generate aldehydes and ketones, respectively.
Reaction mechanism is as follows.
- Pfitzner, K. E.; Moffatt, J. G. (1963). "A New and Selective Oxidation of Alcohols". J. Am. Chem. Soc. 85: 3027. doi:10.1021/ja00902a036.
- J. G. Moffatt, “Sulfoxide-Carbodiimide and Related Oxidations” in Oxidation vol. 2, R. L. Augustine, D. J. Trecker, Eds. (Dekker, New York, 1971) pp 1–64.
- Tidwell, T. T. Org. React. 1990, 39, 297–572. (Review)
- Lee, T. V. Comp. Org. Syn. 1991, 7, 291–303. (Review)