Periodinane

Periodinanes also known as λ5-iodanes are organoiodine compounds with iodine in the +5 oxidation state. These compounds are described as hypervalent because the iodine center has more than 8 valence electrons.

The Dess-Martin periodinane

Periodinane compounds

The λ5-iodanes such as the Dess-Martin periodinane have square pyramidal geometry with 4 heteroatoms in basal positions and one apical phenyl group.[1]

Iodoxybenzene or iodylbenzene, C6H5IO2, is a known oxidizing agent.

Dess-Martin periodinane (1983) is another powerful oxidant and an improvement of the IBX acid already in existence in 1983. The IBX acid is prepared from 2-iodobenzoic acid and potassium bromate and sulfuric acid [2] and is insoluble in most solvents whereas the Dess-Martin reagent prepared from reaction of the IBX acid with acetic anhydride is very soluble. The oxidation mechanism ordinarily consists of a ligand exchange reaction followed by a reductive elimination.


Uses

The predominant use of periodinanes is as oxidizing reagents replacing toxic reagents based on heavy metals.[3]

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See also

References
  1. Boeckman, Robert J.; George, Kelly M. (2009). "1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one". Encyclopedia of Reagents for Organic Synthesis. doi:10.1002/047084289X.rt157m.pub2.
  2. Robert K. Boeckman, Jr., Pengcheng Shao, and Joseph J. Mullins. "1,2-Benziodoxol-3(1H)-one, 1,1,1-tris(acetyloxy)-1,1-dihydro-". Organic Syntheses.CS1 maint: multiple names: authors list (link); Collective Volume, 10, p. 696
  3. Hypervalent iodine(V) reagents in organic synthesis Uladzimir Ladziata and Viktor V. Zhdankin Arkivoc 05-1784CR pp 26-58 2006 Article
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