Pfitzner-Moffatt oxidation

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The Pfitzner-Moffatt oxidation is a chemical reaction which describes the oxidation of primary and secondary alcohols by reaction with dicyclohexylcarbodiimide (DCC) and dimethyl sulfoxide (DMSO). 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.

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

[edit] References

  1. ↑  Pfitzner, K. E.; Moffatt, J. G. J. Am. Chem. Soc. 1963, 85, 3027.
  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)

[edit] See also

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