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Synthesis 2005(2): 286-290  
DOI: 10.1055/s-2004-834940
PAPER
© Georg Thieme Verlag Stuttgart · New York

Three-Component Reactions of Halogenotrinitromethanes with Alkenes

Ekaterina M. Budynina, Olga A. Ivanova, Elena B. Averina, Yurii K. Grishin, Tamara S. Kuznetsova*, Nikolai S. Zefirov
Moscow State University, Chemistry Department, Leninskie gory, 119992 Moscow, Russia
Fax: +7(095)9390290; e-Mail: kuzn@org.chem.msu.ru;
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Publication History

Received 2 July 2004
Publication Date:
01 December 2004 (online)

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Abstract

Three-component one-pot reactions of bromotrinitromethane with bicyclobutylidene and methylenecyclobutanes provide a simple route to halogen-substituted isoxazolidines of mixed composition. With these same olefins, iodotrinitromethane gives adducts which decomposed rapidly to yield the corresponding isoxazolines. Reaction of bromotrinitromethane and bicyclobutylidene with electron-deficient alkenes produced isoxazolidines together with bromotrinitroalkanes as side products.

Key words

multi-component reaction - cycloaddition - heterocycles - small ring systems - polynitro compounds

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4

The scope of the stated method is restricted to nucleophilic and hindered olefins like tri- and tetrasubstituted alkyl or aryl cycloalkenes, which form nitronic esters in situ. For analogues see ref.3