Corey-Kim Oxidation

E. J. Corey, C. U. Kim, J. Am. Chem. Soc. 94, 7586 (1972).

Oxidation of primary and secondary alcohols via their alkoxysulfonium salts. Upon the addition of base, the salt rearranges intramolecularly to aldehydes and ketones, respectively:



Application to the synthesis of α-hydroxy ketones: E. J. Corey, C. U. Kim, Tetrahedron Letters 1974, 287; of 1,3-dicarbonyl compounds: S. Katayama et al., Synthesis 1988, 178; J. T. Pulkkinen et al., J. Org. Chem. 61, 8604 (1996). Cf. Pfitzner-Moffatt Oxidation; Swern Oxidation.