Malaprade Reaction (Periodic Acid Oxidation)

L. Malaprade, Bull. Soc. Chim. France [4] 43, 683 (1928); Compt. Rend. 186, 382 (1928).

Compounds containing two hydroxyl groups, or a hydroxyl and an amino group, attached to adjacent carbon atoms, undergo cleavage of the carbon-carbon bond when treated with periodic acid to yield aldehydes:

H. O. House, Modern Synthetic Reactions (W. A. Benjamin, Menlo Park, California, 2nd ed., 1972) pp 353-359; 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 177-185. Cf. Criegee Reaction.