Email this article Transformations of gem-dibromoarylcyclopropanes under nitrosation conditions on treatment with NOCl·(SO3)n
- Authors: Bondarenko O.B.1, Gavrilova A.Y.1, Nikolaeva S.N.1, Zyk N.V.1,2
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Affiliations:
- Department of Chemistry, M. V. Lomonosov Moscow State University
- Institute of Physiologically Active Compounds, Russian Academy of Sciences
- Issue: Vol 65, No 5 (2016)
- Pages: 1225-1231
- Section: Full Articles
- URL: https://journals.rcsi.science/1066-5285/article/view/238064
- DOI: https://doi.org/10.1007/s11172-016-1439-3
- ID: 238064
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Abstract
The reaction of 2-aryl-1,1-dibromocyclopropanes with adduct NOCl·(SO3)n leading to 3-aryl-5-bromoisoxazoles as a result of nitrosation—heterocyclization of the cyclopropane ring was studied. The reaction is accompanied with electrophilic aromatic bromination. The mechanism of the transformation was discussed, the optimal reaction conditions to enhance the reaction selectivity were developed.
About the authors
O. B. Bondarenko
Department of Chemistry, M. V. Lomonosov Moscow State University
Author for correspondence.
Email: bondarenko@org.chem.msu.ru
Russian Federation, 1 Leninskie Gory, Moscow, 119992
A. Yu. Gavrilova
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bondarenko@org.chem.msu.ru
Russian Federation, 1 Leninskie Gory, Moscow, 119992
S. N. Nikolaeva
Department of Chemistry, M. V. Lomonosov Moscow State University
Email: bondarenko@org.chem.msu.ru
Russian Federation, 1 Leninskie Gory, Moscow, 119992
N. V. Zyk
Department of Chemistry, M. V. Lomonosov Moscow State University; Institute of Physiologically Active Compounds, Russian Academy of Sciences
Email: bondarenko@org.chem.msu.ru
Russian Federation, 1 Leninskie Gory, Moscow, 119992; 1 Severnyi proezd, Chernogolovka, Moscow Region, 142432
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