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https://hdl.handle.net/10316/5167
Title: | Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2-carboxylates | Authors: | Pinho e Melo, Teresa M. V. D. Cardoso, Ana L. Gonsalves, António M. d'A. Rocha |
Keywords: | dehalogenation; 2-halo-2H-azirine-2-carboxylates; chiral 2H-azirine-2-carboxylates | Issue Date: | 2003 | Citation: | Tetrahedron. 59:13 (2003) 2345-2351 | Abstract: | The dehalogenation of 2-halo-3-phenyl-2H-azirine-2-carboxylates is described. Using sodium borohydride and tributyltin hydride 3-phenyl-2H-azirine-2-carboxylates were obtained in moderate yields. The synthesis of a new 2-bromo-2H-azirines with a chiral auxiliary, 10-phenylsulfonylisobornyl 2-bromo-3-phenyl-2H-azirine-2-carboxylate, is reported. Its dehalogenation led to 10-phenylsulfonylisobornyl 2H-azirine-2-carboxylate as single stereoisomer together with the formation of 10-phenylsulfonylisobornyl acetate. | URI: | https://hdl.handle.net/10316/5167 | DOI: | 10.1016/s0040-4020(03)00248-5 | Rights: | openAccess |
Appears in Collections: | FCTUC Química - Artigos em Revistas Internacionais |
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