A Mechanistic Study for Aziridination of Nitroalkenes Mediated by N-Chlorosuccinimide

Direct aziridination of a nitrostyrene is achieved upon treatment with an alkylamine and N-chlorosuccinimide. The reaction is initiated by the Michael addition of amine to nitroalkene. Subsequent N-chlorination and nucleophilic substitution at the nitrogen atom afford 1-alkyl-2-nitroaziridine diaste...

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Bibliographic Details
Published in:Journal of Oleo Science 2022, Vol.71(6), pp.897-903
Main Authors: Iwai, Kento, Wada, Khimiya, Hao, Feiyue, Asahara, Haruyasu, Nishiwaki, Nagatoshi
Format: Article
Language:English
Subjects:
Alkylamines
chloramine
intramolecular nucleophilic substitution
nitroalkene
nitroaziridine
Nitrogen
NMR
Nuclear magnetic resonance
Reaction mechanisms
Substitution reactions
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Summary:Direct aziridination of a nitrostyrene is achieved upon treatment with an alkylamine and N-chlorosuccinimide. The reaction is initiated by the Michael addition of amine to nitroalkene. Subsequent N-chlorination and nucleophilic substitution at the nitrogen atom afford 1-alkyl-2-nitroaziridine diastereoselectively. This reaction mechanism was clarified by NMR studies.
ISSN:1345-8957
1347-3352
DOI:10.5650/jos.ess21406