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 stereochem...

Full description

Saved in:
Bibliographic Details
Published inOrganic letters Vol. 1; no. 13; pp. 2125 - 2128
Main Authors Asensio, Gregorio, Andreu, Cecilia, Boix-Bernardini, Carmen, Mello, Rossella, González-Nuñez, María Elena
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 30.12.1999
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
SYN-ELIMINATION
REARRANGEMENT
ASSISTED NUCLEOPHILIC-SUBSTITUTION
METHYL(TRIFLUOROMETHYL)DIOXIRANE
CHEMISTRY
IODINE
INTERMEDIATE
OXYFUNCTIONALIZATION
PERACID OXIDATION
ALKYL IODIDES
Online AccessGet full text

Cover

More Information
Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol9903281