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Malaprade reaction

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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. 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).

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. L. Malaprade (1928). "Action of polyalcohols on periodic acid". Bull. Soc. Chim. France. 43: 683.
  4. L. Malaprade (1928). "Oxidation of some polyalcohols by periodic acid-applications". Compt. Rend. 186: 382.
  5. 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.
  6. 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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