In organic chemistry, the Malaprade reaction or Malaprade oxidation is a glycol cleavage reaction in which a vicinal diol is oxidized by periodic acid or a periodate salt to give the corresponding carbonyl functional groups.[1][2] The reaction was first reported by Léon Malaprade in 1928.[3][4] Amino alcohols are also cleaved.[5]
In terms of mechanism, the reaction is thought to proceed by a cyclic diester of iodine(VII).[6]
See also
References
- ^ Christopher R. Schmid, Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Organic Syntheses. 72: 6. doi:10.15227/orgsyn.072.0006.
- ^ "406. Malaprade Reaction (Malaprade Oxidation)". Comprehensive Organic Name Reactions and Reagents. Wiley. 2010. pp. 1807–1810. doi:10.1002/9780470638859.conrr406.
- ^ L. Malaprade (1928). "Action of polyalcohols on periodic acid". Bull. Soc. Chim. France. 43: 683.
- ^ L. Malaprade (1928). "Oxidation of some polyalcohols by periodic acid-applications". Compt. Rend. 186: 382.
- ^ Nicolet, Ben H.; Shinn, Leo A. (1939). "The action of periodic acid on α-amino alcohols". Journal of the American Chemical Society. 61 (6): 1615. doi:10.1021/ja01875a521.
- ^ Smith, Michael B.; March, Jerry (2007), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (6th ed.), New York: Wiley-Interscience, p. 1732-1734, ISBN 978-0-471-72091-1
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