Malaprade reaction explained

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).

See also

• Criegee oxidation

Notes and References

1. Christopher R. Schmid, Jerry D. Bryant. 10.15227/orgsyn.072.0006 . D-(R)-Glyceraldehyde Acetonide . Organic Syntheses . 1995 . 72 . 6 .
2. Book: Comprehensive Organic Name Reactions and Reagents. 406. Malaprade Reaction (Malaprade Oxidation) . 1807–1810 . 10.1002/9780470638859.conrr406 . Wiley . 2010 .
3. L. Malaprade. Bull. Soc. Chim. France. 43. 683. 1928 . Action of polyalcohols on periodic acid.
4. L. Malaprade. Compt. Rend.. 186. 382. 1928 . Oxidation of some polyalcohols by periodic acid-applications.
5. 10.1021/ja01875a521 . The action of periodic acid on α-amino alcohols . 1939 . Nicolet . Ben H. . Shinn . Leo A. . Journal of the American Chemical Society . 61 . 6 . 1615 .