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Pfitzner-Moffatt oxidation
Introduction
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.[1][2]
This reaction has been largely abandoned for the Swern oxidation, which gives higher yields with fewer side products.
Several reviews have been published.[3][4]
References
References
- ↑ 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)