Aziridines, 61 [1]: Ring Opening of 2,2-Dimethyl-1-sulfonylaziridines by Anilines: Regioselectivity and Revised Structure of Main Products

Berthold Buchholz Buchholz, Andreas Onistschenko Onistschenko, Helmut Stamm Stamm, Pen Yuan Lin

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

It is shown (1) that in most reactions of anilines 2 with 1-sulfonyl-2,2-dim ethylaziridines 1 both isomeric products 3 and 4 are formed, (2) that the “normal” product 4 obtained by attack on position 3 of 1 usually arises in a small or negligible amount that seems to decrease with decreasing basicity of 2, and (3) that the amount of 4 strongly increases w ith increasing steric demand of 2. Formation of 4 is explained by a lag of bond making in SN2.

Original languageEnglish
Pages (from-to)483-487
Number of pages5
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume48
Issue number4
DOIs
Publication statusPublished - Apr 1 1993
Externally publishedYes

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Keywords

  • 1-Sulfonyl-2,2-dim ethylaziridines
  • Basicity Effect
  • N-Aryl-N′-sulfonyl-gem-dimethylethylenediamines
  • Regioselectivity of Nucleophilic Ring Opening
  • Steric Hindrance Effect

ASJC Scopus subject areas

  • Chemistry(all)

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