Iodomethane Oxidation by Dimethyldioxirane:  A New Route to Hypoiodous Acid and Iodohydrines

The oxidation of iodomethane with dimethyldioxirane allows the generation of stable neutral solutions of hypoiodous acid in the absence of any trapping agent for iodide anion. Hypoiodous acid is trapped in situ by addition to representative olefins to give iodohydrines in good yields. The stereochemical study of the products shows the <i>anti</i>-stereospecific nature of the iodohydroxylation reaction.