Pfitzner-Moffatt oxidation

Pfitzner-Moffatt oxidation

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. [cite journal | author = Pfitzner, K. E.; Moffatt, J. G. | journal = J. Am. Chem. Soc. | year = 1963 | volume = 85 | pages = 3027 | doi = 10.1021/ja00902a036 | title = A New and Selective Oxidation of Alcohols] [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.]

This reaction has been largely abandoned for the Swern oxidation, which gives higher yields with fewer side products.

Several reviews have been published. [Tidwell, T. T. "Org. React." 1990, "39", 297-572. (Review)] [Lee, T. V. "Comp. Org. Syn." 1991, "7", 291-303. (Review)]

References

ee also

* Corey-Kim oxidation
* Swern oxidation


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