Regioselective 1,2-hydroxy and methoxy iodination of alkenes by molecular iodine and aqueous hydrogen peroxide

Treatment of an alkene with iodine and aqueous hydrogen peroxide (30%) in acetonitrile gives the corresponding hydroxy-iodoalkane regioselectively in high yield. On the other hand the same reaction in methanol gives methoxyiodoalkanes in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.

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Bibliographic Details
Published inTetrahedron letters Vol. 47; no. 12; pp. 1997 - 2001
Main Authors Raju, BR, Kumar, EKP, Saikia, AK
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 20.03.2006
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIDATION
HALIDES
ROUTE
iodohydroxylation
ACID
hydrogen peroxide
VICINAL ALKOXYIODOALKANES
regioselective
EPOXIDES
BETA-HALOHYDRINS
iodomethoxylation
iodine
ACETATE
aqueous
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Summary:Treatment of an alkene with iodine and aqueous hydrogen peroxide (30%) in acetonitrile gives the corresponding hydroxy-iodoalkane regioselectively in high yield. On the other hand the same reaction in methanol gives methoxyiodoalkanes in excellent yield. (c) 2006 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2006.01.064