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

Daniel Winkelhaus; Michael H. Holthausen; Roman Dobrovetsky; Douglas W. Stephan

doi:10.1039/C5SC02336J

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

Daniel Winkelhaus,‡^a Michael H. Holthausen,‡^a Roman Dobrovetsky^b and Douglas W. Stephan*^a

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* Corresponding authors

^a Department of Chemistry, University of Toronto, 80 St. George St, Toronto, Ontario M5S3H6, 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.

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Article information

DOI: https://doi.org/10.1039/C5SC02336J
Article type: Edge Article
Submitted: 28 Jun 2015
Accepted: 20 Jul 2015
First published: 21 Jul 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry

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Chem. Sci., 2015,6, 6367-6372

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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

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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