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Title: | Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction | Authors: | Cardoso, Ana L. Sousa, Carmo Henriques, Marta S. C. Paixão, J. A. Melo, Teresa M. V. D. Pinho e |
Keywords: | 2-halo-2H-azirines; vinyl tetrazoles; tetrasubstituted alkenes; phosphorus ylides | Issue Date: | 12-Dec-2015 | Publisher: | MDPI | Project: | UID/QUI/00313/2013 post-doctoral research grant CQC-QO-BPD-2015 |
Serial title, monograph or event: | Molecules | Volume: | 20 | Issue: | 12 | 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. | URI: | https://hdl.handle.net/10316/109235 | ISSN: | 1420-3049 | DOI: | 10.3390/molecules201219848 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais FCTUC Física - Artigos em Revistas Internacionais I&D CFis - Artigos em Revistas Internacionais I&D CQC - Artigos em Revistas Internacionais |
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Synthesis-of-New-2Halo21Htetrazol5yl2Hazirines-via-a-NonClassical-Wittig-ReactionMolecules.pdf | 2.32 MB | Adobe PDF | View/Open |
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