6533b82cfe1ef96bd128f3f5

RESEARCH PRODUCT

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

Cecilia AndreuCarmen Boix-bernardiniAnd Rossella MelloMaría Elena González NúñezGregorio Asensio

subject

chemistry.chemical_classificationchemistry.chemical_compoundchemistryOrganic ChemistryIodideOrganic chemistryPhysical and Theoretical ChemistryDimethyldioxiranePhotochemistryBiochemistryHypoiodous acid

description

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 anti-stereospecific nature of the iodohydroxylation reaction.

https://doi.org/10.1021/ol9903281