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Issue 11, 2015
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Phosphine and carbene azido-cations: [(L)N3]+ and [(L)2N3]+

Daniel Winkelhaus,a  Michael H. Holthausen,a  Roman Dobrovetskyb  and  Douglas W. Stephan*a 
Author affiliations

* Corresponding authors

a Department of Chemistry, University of Toronto, 80 St. George St, Toronto, Canada
E-mail: dstephan@chem.utoronto.ca

b School of Chemistry, Raymond and Beverly Sackler Faculty of Exact Sciences, Tel Aviv University, Tel Aviv 69978, Israel

Abstract

The cationic N3-species [(p-HC6F4)3PN3]+ (1) featuring a perfluoro-arene phosphonium group serves as a N3+-source in stoichiometric reactions with several Lewis bases (L) allowing for the stepwise formation of [(L)N3]+ and [(L)2N3]+ cations (L = phosphine, carbene) with liberation of (p-HC6F4)3P. X-Ray diffraction analysis and computational studies provide insight into the bonding in these remarkably stable azido-cations.

Graphical abstract: Phosphine and carbene azido-cations: [(L)N3]+ and [(L)2N3]+

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Publication details

The article was received on 28 Jun 2015, accepted on 20 Jul 2015 and first published on 21 Jul 2015


Article type: Edge Article
DOI: 10.1039/C5SC02336J
Citation: Chem. Sci., 2015,6, 6367-6372
  • Open access: Creative Commons BY license
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    Phosphine and carbene azido-cations: [(L)N3]+ and [(L)2N3]+

    D. Winkelhaus, M. H. Holthausen, R. Dobrovetsky and D. W. Stephan, Chem. Sci., 2015, 6, 6367
    DOI: 10.1039/C5SC02336J

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