Literature DB >> 35584955

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

Kento Iwai1,2, Khimiya Wada1, Feiyue Hao1,3, Haruyasu Asahara1,2,4, Nagatoshi Nishiwaki1,2.   

Abstract

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.

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Keywords:  chloramine; intramolecular nucleophilic substitution; nitroalkene; nitroaziridine

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Year:  2022        PMID: 35584955     DOI: 10.5650/jos.ess21406

Source DB:  PubMed          Journal:  J Oleo Sci        ISSN: 1345-8957            Impact factor:   1.601


  1 in total

1.  Unusual Reactivities of ortho-Hydroxy-β-nitrostyrene.

Authors:  Kento Iwai; Khimiya Wada; Nagatoshi Nishiwaki
Journal:  Molecules       Date:  2022-07-27       Impact factor: 4.927

  1 in total

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