Pfitzner–Moffatt oxidation

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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]

The Pfitzner–Moffatt oxidation

This reaction has been largely abandoned for the Swern oxidation, which gives higher yields with fewer side products. The Moffatt oxidation yields urea biproducts that are often difficult to remove.

Several reviews have been published.[3][4]

Reaction mechanism is as follows.

Pfitzner-moffatt.png

See also[edit]

References[edit]

  1. ^ Pfitzner, K. E.; Moffatt, J. G. (1963). "A New and Selective Oxidation of Alcohols". J. Am. Chem. Soc. 85: 3027. doi:10.1021/ja00902a036. 
  2. ^ 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.
  3. ^ Tidwell, T. T. Org. React. 1990, 39, 297–572. (Review)
  4. ^ Lee, T. V. Comp. Org. Syn. 1991, 7, 291–303. (Review)