Periodinane
Periodinanes also known as λ5-iodanes are organoiodine compounds with iodine in the +5 oxidation state.
These compounds are hypervalent because the iodine atoms in them formally contain more than 8 valence electrons.
The λ5-iodanes such as the Dess-Martin periodinane have square pyramidal geometries with 4 heteroatoms in basal positions and one apical phenyl group.
Iodoxybenzene or iodylbenzene, C6H5IO2, is a known oxidizing agent. It was first prepared by Willgerodt by disproportionation of iodosylbenzene under steam distillation to iodylbenzene and iodobenzene:
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 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.
The predominant use of periodinanes is as oxidizing reagents replacing toxic reagents based on heavy metals.
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