Regio- and stereoselective hydroxybromination and dibromination of olefins using ammonium bromide and oxone

An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio- and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov’s rule, using eco-friendly, non-toxic, and stable reagents such as NH4...

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Bibliographic Details
Published inTetrahedron letters Vol. 53; no. 11; pp. 1401 - 1405
Main Authors Macharla, Arun Kumar, Chozhiyath Nappunni, Rohitha, Nama, Narender
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 14.03.2012
Elsevier
Subjects
Alkenes
Chemistry
Chemistry, Organic
Dibromination
Hydroxybromination
Physical Sciences
Regioselectivity
Science & Technology
Stereoselectivity
Stereoselectivity
Hydroxybromination
Alkenes
Regioselectivity
Dibromination
BROMOHYDRINS
CONVERSION
CLEAVAGE
OXIDATIVE BROMINATION
EPOXIDES
CATALYTIC ASYMMETRIC EPOXIDATION
IODOHYDRIN
DERIVATIVES
CARBOXYLIC-ACIDS
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Summary:An efficient protocol for the synthesis of vicinal bromohydrins and dibromides from olefins is presented. Various olefins are regio- and stereoselectively hydroxybrominated and dibrominated with anti fashion, following Markonikov’s rule, using eco-friendly, non-toxic, and stable reagents such as NH4Br and oxone® in CH3CN/H2O (1:1) and CH3CN without employing catalyst in moderate to excellent yields. Bromohydrins are formed instantaneously.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2012.01.026