Synthesis of New 2-Halo-2-1H-tetrazol-5-yl-2H-azirines via a Non-Classical Wittig ReactionReport as inadecuate




Synthesis of New 2-Halo-2-1H-tetrazol-5-yl-2H-azirines via a Non-Classical Wittig Reaction - Download this document for free, or read online. Document in PDF available to download.

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

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





Author: Ana L. Cardoso 1, Carmo Sousa 1, Marta S. C. Henriques 2, José A. Paixão 2 and Teresa M. V. D. Pinho e Melo 1,*

Source: http://mdpi.com/



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