86. 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:

Chemical reaction

References

Application to the synthesis of α-hydroxy ketones: E. J. Corey, C. U. Kim, Tetrahedron Lett. 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.