Phosphorylation of 2-azabicyclo[2.2.1]hept-5-ene and 2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene systems: synthesis and mechanistic study

• Tipo: Artigo em Revista Científica Internacional
• Data: 2010

Autores

Carlos A D Sousa (Autor) Outra; Luisa L C Vale (Autor) FCUP; Jose E Rodriguez Borges (Autor) FCUP; Xerardo Garcia Mera (Autor) Outra

Revista

Título: New Journal of Chemistry

Vol. 34 Nº 11

Páginas: 2546-2551

ISSN: 1144-0546

Editora: Royal Society of Chemistry

Indexação

ISI Web of Knowledge - 7 Citações

Scopus - 7 Citações

Classificação Científica

FOS: Ciências exactas e naturais > Química

Outras Informações

ID Authenticus: P-003-C3S

DOI: 10.1039/c0nj00239a

Abstract (EN): The endo and exo isomers of (+/-)-methyl 2-hydroxy-2-azabicyclo[2.2.1]hept-5-ene-3-carboxylates and the in situ-prepared endo and exo isomers of (+/-)-methyl 2-azabicyclo[2.2.1]hept-5-ene-3-carboxylate were treated with diphenylphosphinic chloride (OPClPh(2)) and chlorodiphenylphosphine (ClPPh(2)) to afford the corresponding phosphorylated bicycles. The structure of all these compounds was unequivocally determined by NMR spectroscopy and mass spectrometry, and, based on the results obtained, a mechanistic scheme for the phosphorylation reaction of these adducts to afford the corresponding phosphorylbicycles is proposed.

Idioma: Inglês

Tipo (Avaliação Docente): Científica

Nº de páginas: 6