{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,24]],"date-time":"2026-09-24T23:47:47Z","timestamp":1790293667805,"version":"4.1.0"},"reference-count":38,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2015,12,12]],"date-time":"2015-12-12T00:00:00Z","timestamp":1449878400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"FCT","doi-asserted-by":"publisher","award":["UID\/QUI\/00313\/2013"],"award-info":[{"award-number":["UID\/QUI\/00313\/2013"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"FCT","doi-asserted-by":"publisher","award":["CQC-QO-BPD-2015"],"award-info":[{"award-number":["CQC-QO-BPD-2015"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>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.<\/jats:p>","DOI":"10.3390\/molecules201219848","type":"journal-article","created":{"date-parts":[[2015,12,14]],"date-time":"2015-12-14T02:57:29Z","timestamp":1450061849000},"page":"22351-22363","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction"],"prefix":"10.3390","volume":"20","author":[{"given":"Ana","family":"Cardoso","sequence":"first","affiliation":[{"name":"Centro de Qu\u00edmica de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Carmo","family":"Sousa","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9202-0847","authenticated-orcid":false,"given":"Marta","family":"Henriques","sequence":"additional","affiliation":[{"name":"CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jos\u00e9","family":"Paix\u00e3o","sequence":"additional","affiliation":[{"name":"CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3256-4954","authenticated-orcid":false,"given":"Teresa","family":"Pinho e Melo","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2015,12,12]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"3363","DOI":"10.1016\/j.tet.2013.02.020","article-title":"Recent advances in 2H-azirine chemistry","volume":"69","author":"Khlebnikov","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_2","unstructured":"Maes, B.U.W., Cossy, J., and Slovenko, P. 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