308. Pfitzner-Moffatt Oxidation

(Moffatt Oxidation)

K. E. Pfitzner, J. G. Moffatt, J. Am. Chem. Soc. 85, 3027 (1963).

Mild oxidation of primary and secondary alcohols, promoted by dicyclohexylcarbodiimide activation of dimethyl sulfoxide, evidently involving the alkoxysulfonium ylides, which rearrange intramolecularly to generate aldehydes and ketones, respectively:

Chemical reaction

References

Reviews: 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; T. T. Tidwell, Org. React. 39, 297-572 passim (1990); T. V. Lee, Comp. Org. Syn. 7, 291-303 passim (1991). Cf. Corey-Kim Oxidation; Swern Oxidation.