Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction
AbstractThe 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
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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.
Cardoso AL, Sousa C, Henriques MSC, Paixão JA, Pinho e Melo TMVD. Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction. Molecules. 2015; 20(12):22351-22363.Chicago/Turabian Style
Cardoso, Ana L.; Sousa, Carmo; Henriques, Marta S.C.; Paixão, José A.; Pinho e Melo, Teresa M.V.D. 2015. "Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction." Molecules 20, no. 12: 22351-22363.