title: Synthesis of New 2-Halo-2-(1H-tetrazol-5-yl)-2H-azirines via a Non-Classical Wittig Reaction.
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.
authors.affiliation: Centro de Química de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal. analcclopes@gmail.com.
authors.forename: Ana L
authors.initials: AL
authors.lastname: Cardoso
authors.affiliation: Centro de Química de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal. carmo.b.sousa@gmail.com.
authors.forename: Carmo
authors.initials: C
authors.lastname: Sousa
authors.affiliation: CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal. marta.henriques@gmail.com.
authors.forename: Marta S C
authors.initials: MS
authors.lastname: Henriques
authors.affiliation: CFisUC and Department of Physics, University of Coimbra, Coimbra P-3004-516, Portugal. jap@fis.uc.pt.
authors.forename: José A
authors.initials: JA
authors.lastname: Paixão
authors.affiliation: Centro de Química de Coimbra and Department of Chemistry, University of Coimbra, Coimbra 3004-535, Portugal. tmelo@ci.uc.pt.
authors.forename: Teresa M V D
authors.initials: TM
authors.lastname: Pinho e Melo
mesh_terms: D001389:Azirines / Q000737:chemistry*; D018360:Crystallography, X-Ray / Q000379:methods; D015394:Molecular Structure; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D001389:Azirines; D013777:Tetrazoles; C045574:1H-tetrazole
keywords: 2-halo-2H-azirines; phosphorus ylides; tetrasubstituted alkenes; vinyl tetrazoles