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. Amino alcohols are also cleaved.

In terms of mechanism, the reaction is thought to proceed by a cyclic diester of iodine(VII).[3]

See also

References

  1. ^ Christopher R. Schmid, Jerry D. Bryant (1995). "D-(R)-Glyceraldehyde Acetonide". Organic Syntheses. 72: 6. doi:10.15227/orgsyn.072.0006.
  2. ^ "406. Malaprade Reaction (Malaprade Oxidation)". Comprehensive Organic Name Reactions and Reagents. Wiley. 2010. pp. 1807–1810. doi:10.1002/9780470638859.conrr406.
  3. ^ 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

Historic references