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Molecules 2015, 20(12), 22351-22363; doi:10.3390/molecules201219848

Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction

1
Centro de Química de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal
2
CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal
*
Author to whom correspondence should be addressed.
Academic Editor: Klaus Banert
Received: 30 October 2015 / Revised: 30 November 2015 / Accepted: 8 December 2015 / Published: 12 December 2015
(This article belongs to the Special Issue Organic Azides)
View Full-Text   |   Download PDF [2315 KB, uploaded 14 December 2015]   |  

Abstract

The synthesis and reactivity of tetrazol-5-yl-phosphorus ylides towards N-halosuccinimide/TMSN3 reagent systems was explored, opening the way to new haloazidoalkenes bearing a tetrazol-5-yl substituent. These compounds were obtained as single isomers, except in one case. X-ray crystal structures were determined for three derivatives, establishing that the non-classical Wittig reaction leads to the selective synthesis of haloazidoalkenes with (Z)-configuration. The thermolysis of the haloazidoalkenes afforded new 2-halo-2-(tetrazol-5-yl)-2H-azirines in high yields. Thus, the reported synthetic methodologies gave access to important building blocks in organic synthesis, vinyl tetrazoles and 2-halo-2-(tetrazol-5-yl)-2H-azirine derivatives. View Full-Text
Keywords: 2-halo-2H-azirines; vinyl tetrazoles; tetrasubstituted alkenes; phosphorus ylides 2-halo-2H-azirines; vinyl tetrazoles; tetrasubstituted alkenes; phosphorus ylides
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Cardoso, A.L.; Sousa, C.; Henriques, M.S.C.; Paixão, J.A.; Pinho e Melo, T.M.V.D. Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction. Molecules 2015, 20, 22351-22363.

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