A New Approach to the Synthesis of Vicinal Iodoperoxyalkanes by the Reaction of Alkenes with Iodine and Hydroperoxides

Alexander O. Terent’ev; Igor B. Krylov; Dmitry A. Borisov; Gennady I. Nikishin

doi:10.1055/s-2007-990776

PAPER

A New Approach to the Synthesis of Vicinal Iodoperoxyalkanes by the Reaction of Alkenes with Iodine and Hydroperoxides

Alexander O. Terent’ev*, Igor B. Krylov, Dmitry A. Borisov, Gennady I. Nikishin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp., Moscow 119991, Russian Federation
Fax: +7(495)1355328; e-Mail: terentev@ioc.ac.ru;

Abstract

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Abstract

A convenient procedure was developed for the synthesis of vicinal iodoperoxyalkanes by the reaction of alkenes with iodine and hydroperoxides. The best results were achieved with the use of excess iodine. The replacement of one iodine atom by hydroperoxides in vicinal diiodoalkanes was discovered. A suggestion was made about the reaction mechanism.

Key words

iodination - peroxidation - hydrogen peroxide - tert-butyl hydroperoxide - iodoperoxyalkanes

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