Reaction of Enol Ethers with
the I2-H2O2 System: Synthesis
of 2-Iodo-1-methoxy Hydroperoxides and Their Deperoxidation
and Demethoxylation to 2-Iodo Ketones

Alexander O. Terent’ev; Alexander M. Borisov; Maxim M. Platonov; Zoya A. Starikova; Vladimir V. Chernyshev; Gennady I. Nikishin

doi:10.1055/s-0029-1217062

PAPER

Reaction of Enol Ethers with the I₂-H₂O₂ System: Synthesis of 2-Iodo-1-methoxy Hydroperoxides and Their Deperoxidation and Demethoxylation to 2-Iodo Ketones

Alexander O. Terent’ev*, Alexander M. Borisov, Maxim M. Platonov, Zoya A. Starikova, Vladimir V. Chernyshev, Gennady I. Nikishin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: terentev@ioc.ac.ru;

Abstract

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Abstract

The reaction of enol ethers with the I₂-H₂O₂ system in diethyl ether affords 2-iodo ketones and the previously unknown 2-iodo-1-methoxy hydroperoxides. In the presence of the I₂-H₂O₂ system, the latter compounds undergo deperoxidation and demethoxylation to form 2-iodo ketones. The reaction conditions were found for the synthesis of 2-iodo ketones from enol ethers in 67-94% yields.

Key words

enol ethers - hydrogen peroxide - iodine - peroxides - peroxidation

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Reaction of Enol Ethers with the I2-H2O2 System: Synthesis of 2-Iodo-1-methoxy Hydroperoxides and Their Deperoxidation and Demethoxylation to 2-Iodo Ketones

Reaction of Enol Ethers with the I₂-H₂O₂ System: Synthesis of 2-Iodo-1-methoxy Hydroperoxides and Their Deperoxidation and Demethoxylation to 2-Iodo Ketones