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

• Autor(a) principal: Cardoso, Ana L.
• Data de Publicação: 2015
• Outros Autores: Sousa, Carmo, Henriques, Marta S. C., Paixão, J. A., Melo, Teresa M. V. D. Pinho e
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
• Texto Completo: http://hdl.handle.net/10316/109235; https://doi.org/10.3390/molecules201219848
• topic: 2-halo-2H-azirines; vinyl tetrazoles; tetrasubstituted alkenes; phosphorus ylides; Azirines; Crystallography, X-Ray; Molecular Structure; Stereoisomerism; Tetrazoles

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.