Iodomethane oxidation by dimethyldioxirane: A new route to hypoiodous acidand iodohydrines

Citation
G. Asensio et al., Iodomethane oxidation by dimethyldioxirane: A new route to hypoiodous acidand iodohydrines, ORG LETT, 1(13), 1999, pp. 2125-2128
Citations number
41
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
1
Issue
13
Year of publication
1999
Pages
2125 - 2128
Database
ISI
SICI code
1523-7060(199912)1:13<2125:IOBDAN>2.0.ZU;2-U
Abstract
[GRAPHICS] The oxidation of iodomethane with dimethyldioxirane allows the generation o f stable neutral solutions of hypoiodous acid in the absence of any trappin g agent for iodide anion. Hypoiodous acid is trapped in situ by addition to representative olefins to give iodohydrines in good yields. The stereochem ical study of the products shows the anti-stereospecific nature of the iodo hydroxylation reaction.