Criegee Reaction

R. Criegee, Ber. 64, 260 (1931).

Oxidative cleavage of vicinal glycols by lead tetraacetate:

Reviews: R. Criegee in Newer Methods of Preparative Organic Chemistry vol. 1 (Interscience, New York, 1948) pp 12-20; H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 359-387; K. W. Bentley in Elucidation of Organic Structures by Physical and Chemical Methods pt. 2, K. W. Bentley, G. W. Kirby, Eds. (Wiley, New York, 2nd ed., 1973) pp 169-177; S. Hatakeyama, H. Akimoto, Res. Chem. Intermed. 20, 503-524 (1994). Mechanism: S. Chandrasekhar, C. D. Roy, J. Chem. Soc. Perkin Trans. II 1994, 2141; R. Ponec et al., J. Org. Chem. 62, 2757 (1997); R. M. Goodman, Y. Kishi, J. Am. Chem. Soc. 120, 9392 (1998). Cf. Malaprade Reaction.