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Dess-Martin periodinane



Dess-Martin periodinane
IUPAC name 1,1,1-Triacetoxy-1,1-dihydro-
1,2-benziodoxol-3(1H)-one
Other names Dess-Martin periodinane
Identifiers
CAS number 87413-09-0
SMILES O=C2C1=CC=CC=C1I
(OC(C)=O)(OC(C)=O)
(OC(C)=O)O2
Properties
Molecular formula C13H13IO8
Molar mass 424.14 g/mol
Appearance white powder, chips,
crystals or crystalline
powder and/or chunks
Density 1.362 g/cm3 solid
Melting point

103 - 133 °C

Related Compounds
Related compounds 2-Iodoxybenzoic acid
Except where noted otherwise, data are given for
materials in their standard state
(at 25 °C, 100 kPa)
Infobox disclaimer and references

Dess-Martin periodinane is a chemical reagent used to oxidize primary alcohols to aldehydes and secondary alcohols to ketones.[1][2] This periodinane has several advantages over chromium- and DMSO-based oxidants that include milder conditions, shorter reaction times, higher yields, and simplified workups. It is named after the American chemists Daniel Benjamin Dess and James Cullen Martin.

Contents

Preparation

2-Iodobenzoic acid is oxidized preferably by Oxone, or by KBrO3 to 2-iodoxybenzoic acid. (Caution: 2-Iodoxybenzoic acid has been found to be impact and heat sensitive, decomposing explosively.) [3] The 2-Iodoxybenzoic acid is then treated with a mixture of acetic anhydride, acetic acid and p-toluenesulfonic acid at 80-100 °C for 40 min. The resulted solids can be obtained via filtration and washing with ether.

To avoid the explosive nature of 2-iodoxybenzoic acid, other methods of preparation[4][5] as well as other periodinanes[6] have been described.

Properties and uses

Dess-Martin periodinane is mainly used as an oxidant for complex, sensitive and multifunctional alcohols. One of the reasons for its effectiveness is its high selectivity towards complexation of the hydroxylic group, which allows alcohols to rapidly perform ligand exchange; the first step in the oxidation reaction.

Its effectiveness as an oxidant is also due to its versatility; having a broad scope of being able to convert alcohols to carbonyl derivatives. Its reactions and yield are also known to be clean and high respectively. Work up is also clean and simple. Byproducts from the reaction can be removed easily by precipitation, filtration or chromatography.

References

  1. ^ Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
  2. ^ Boeckman, R. J. In "Encyclopedia of Reagents for Organic Synthesis"; Paquette, L. A., Ed.; Wiley: Chichester, UK, 1995, Vol. 7, pp. 4982-4987. (Review)
  3. ^ Boeckman, Jr., R. K.; Shao, P.; Mullins, J. J. (2004). "The Dess-Martin Periodinane". Org. Synth.; Coll. Vol. 10: 696. 
  4. ^ Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
  5. ^ Meyer, S. D.; Schreiber, S. L. J. Org. Chem. 1994, 59, 7549.
  6. ^ Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277. doi:10.1021/ja00019a027

See also
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Dess-Martin_periodinane". A list of authors is available in Wikipedia.
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