Dess-Martin periodinane
The Dess-Martin periodinane (DMP) is commercially available and decomposes only slowly. But DMP is heat- and shock-sensitive, and shows an exotherm when heated >130 °C. 2-Iodoxybenzoic acid (IBX), the impact-sensitive intermediate in the synthesis of the Dess-Martin periodinane, is available in a DMSO solution and is also used as an oxidizing agent.
Name Reactions
Recent Literature
Partial hydrolysis of DMP or incomplete acetylation gives a more effective
oxidant, explaining why impure samples of DMP in many cases provide better
results than the pure reagent. When reliable and convenient rate enhancement is
desired, pure DMP may be decomposed with an equivalent of water immediately
before or during its use.
S. D. Meyer, S. L. Schreiber, J. Org. Chem., 1994, 59,
7549-7552.
Alcohols are oxidized to the corresponding carbonyl compounds with
iodoxybenzoic acid (IBX) or with Dess-Martin-Periodinane (DMP) in
[bmim]BF4 and [bmim]PF6 ionic liquids at room
temperature in excellent yields with high selectivity. These oxidations are faster in ionic liquids as compared to
conventional solvents. The byproduct
iodosobenzoic acid (IBA) and the ionic liquid are readily recovered.
J. S. Yadav, B. V. S. Reddy, A. K. Basak, A. V.
Narsaiah, Tetrahedron, 2004,
60, 2131-2135.
Among the reported examples of new reactivity of the hypervalent iodine
reagent DMP (Dess-Martin periodinane) are the one-step oxidation of
secondary amides to imides and N-acyl vinylogous carbamates or ureas
and the direct oxidation of benzylic and related primary amines to the
corresponding nitriles.
K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. Int. Ed., 2005,
44, 5992-5997.
K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. Int. Ed., 2005,
44, 5992-5997.
K. C. Nicolaou, C. J. N. Mathison, Angew. Chem. Int. Ed., 2005,
44, 5992-5997.
Dess-Martin periodine in combination with organosulfonic acids reacted with
ketones and dicarbonyl compounds under reflux temperature in acetonitrile to
give α-organosulfonyloxylated compounds in good yields.
U. S. Mahajan, K. G. Akamanchi, Synlett, 2008,
987-990.
A new, mild, and efficient method for the synthesis of 2-substituted
benzothiazoles proceeds via the intramolecular cyclization of
thioformanilides by using hypervalent iodine reagents in CH2Cl2
at ambient temperature.
D. S. Bose, M. Idrees, J. Org. Chem., 2006,
71, 8261-8263.
