Synlett 2012; 23(20): 2943-2946
DOI: 10.1055/s-0032-1317494
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Stable 1H-Azirines Reinvestigated: A Structural Corrigendum

Klaus Banert*
Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany   Fax: +49(371)53121229   Email: klaus.banert@chemie.tu-chemnitz.de
,
Manfred Hagedorn
Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany   Fax: +49(371)53121229   Email: klaus.banert@chemie.tu-chemnitz.de
,
Heiko Peisker
Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany   Fax: +49(371)53121229   Email: klaus.banert@chemie.tu-chemnitz.de
› Author Affiliations
Further Information

Publication History

Received: 21 September 2012

Accepted: 30 September 2012

Publication Date:
09 November 2012 (online)


Abstract

The isoquinoline-catalyzed synthesis of pretended 1H-azirines from phenacyl bromides and N,N′-dialkylcarbodiimides was repeated. The products do not possess the structure of antiaromatic 1H-azirines, but simple N-acyl-N,N′-dialkylureas were formed instead. This structural corrigendum was confirmed by the independent synthesis of the known ureas and comparison of their 1H NMR and 13C NMR spectroscopic data in the case of six compounds. Thus, 1H-azirines keep their classification as very short-lived intermediates.

Supporting Information

 
  • References and Notes


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