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Synthesis 2009(24): 4159-4166  
DOI: 10.1055/s-0029-1217062
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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;
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Publication History

Received 23 July 2009
Publication Date:
19 October 2009 (online)

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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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