Periodinane
Image:Dess-Martin periodinane.svg]]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.
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.{{cite journal |doi=10.1002/047084289X.rt157m.pub2|title=1,1,1-Triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one|journal=Encyclopedia of Reagents for Organic Synthesis|year=2009|last1=Boeckman|first1=Robert J.|last2=George|first2=Kelly M.|isbn=978-0471936237}}
Iodoxybenzene or iodylbenzene, {{chem2|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{{OrgSynth | title = 1,2-Benziodoxol-3(1H)-one, 1,1,1-tris(acetyloxy)-1,1-dihydro- | author = Robert K. Boeckman, Jr., Pengcheng Shao, and Joseph J. Mullins| collvol = 10 | collvolpages = 696 | prep = v77p0141}} 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.Hypervalent iodine(V) reagents in organic synthesis Uladzimir Ladziata and Viktor V. Zhdankin Arkivoc 05-1784CR pp 26-58 2006 [http://www.arkat-usa.org/ark/journal/2006/I09_General/1784/06-1784CR%20as%20published%20mainmanuscript.pdf Article]
See also
References
{{reflist}}
External links
- [https://www.organic-chemistry.org/Highlights/2005/25May.shtm Hypervalent Iodine Chemistry]