Reactivity of 2-halo-2H-azirines. Part 3: Dehalogenation of 2-halo-2H-azirine-2...

• Autor(es): Pinho e Melo, Teresa M. V. D. ; Cardoso, Ana L. ; Rocha Gonsalves, António M. dA.
• Data: 2003
• Identificador Persistente: http://hdl.handle.net/10316/5167
• Origem: Estudo Geral - Universidade de Coimbra
• Assunto(s): dehalogenation; 2-halo-2H-azirine-2-carboxylates; chiral 2H-azirine-2-carboxylates
• Tipo de Documento: Artigo
• Idioma: Inglês

Descrição

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. http://www.sciencedirect.com/science/article/B6THR-482NK06-7/1/b576da25bb07c16918052295f89735c8