This work was supported by the Alexander von Humboldt Foundation in the form of a Feodor-Lynen grant (U.W.), and by the Centre National de la Recherche Scientifique.
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Synthesis of a 2H-Azirine by [1 + 2] Cycloaddition of a Phosphinocarbene with a Nitrile and Its Ring-Expansion to a 1,2λ5-Azaphosphete†
Article first published online: 22 DEC 2003
DOI: 10.1002/anie.199512461
Copyright © 1995 by VCH Verlagsgesellschaft mbH, Germany
Issue
Angewandte Chemie International Edition in English
Volume 34, Issue 11, pages 1246–1248, June 16, 1995
Additional Information
How to Cite
Alcaraz, G., Wecker, U., Baceiredo, A., Dahan, F. and Bertrand, G. (1995), Synthesis of a 2H-Azirine by [1 + 2] Cycloaddition of a Phosphinocarbene with a Nitrile and Its Ring-Expansion to a 1,2λ5-Azaphosphete. Angewandte Chemie International Edition in English, 34: 1246–1248. doi: 10.1002/anie.199512461
- †
Publication History
- Issue published online: 22 DEC 2003
- Article first published online: 22 DEC 2003
- Manuscript Received: 9 JAN 1995
- Abstract
- References
- Cited By
Keywords:
- carbenes;
- cycloadditions;
- heterocycles;
- phosphorus compounds
Graphical Abstract
A new type of carbene reaction is observed with the stable phosphinocarbene 1. It reacts with benzonitrile to give the 2H-azirine 2, which in dichloromethane is converted into the 1,2λ5-azaphosphete 3 after addition of a catalytic amount of dichloro(p-cymene)ruthenium(II). R = (c-C6H11)2N.