Chlorination of Oximes with Aqueous H2O2/HCl System: Facile Synthesis of gem-Chloronitroso- and gem-Chloronitroalkanes, gem-Chloronitroso- and gem-Chloronitrocycloalkanes

Alexander O. Terent’ev; Igor B. Krylov; Yuri N. Ogibin; Gennady I. Nikishin

doi:10.1055/s-2006-950304

PAPER

Chlorination of Oximes with Aqueous H₂O₂/HCl System: Facile Synthesis of gem-Chloronitroso- and gem-Chloronitroalkanes, gem-Chloronitroso- and gem-Chloronitrocycloalkanes

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

Abstract

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Abstract

Chlorination of cyclic and linear ketone oximes with aqueous H₂O₂/HCl in a two-phase dichloromethane-water system selectively affords gem-chloronitroso compounds in yields of up to 94%. One-pot oxidation of the resulting gem-chloronitroso compounds with peracetic acid, prepared in situ, gives gem-chloronitroalkanes and cycloalkanes in yields of up to 82%. The advantages of the method are that it is facile and environmentally benign and does not require gaseous chlorine.

Key words

oximes - gem-chloronitroso compounds - gem-chloronitro compounds - chlorination - oxidation - hydrogen peroxide

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