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Synthesis 2006(22): 3819-3824
DOI: 10.1055/s-2006-950304
DOI: 10.1055/s-2006-950304
PAPER
© Georg Thieme Verlag Stuttgart · New York
Chlorination of Oximes with Aqueous H2O2/HCl System: Facile Synthesis of gem-Chloronitroso- and gem-Chloronitroalkanes, gem-Chloronitroso- and gem-Chloronitrocycloalkanes
Further Information
Received
5 June 2006
Publication Date:
09 October 2006 (online)
Publication History
Publication Date:
09 October 2006 (online)
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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