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

• Type: Article in International Scientific Journal
• Date: 2010

Authors

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

Journal

Title: New Journal of Chemistry

Vol. 34 No. 11

Pages: 2546-2551

ISSN: 1144-0546

Publisher: Royal Society of Chemistry

Indexing

ISI Web of Knowledge - 7 Citations

Scopus - 7 Citations

Scientific classification

FOS: Natural sciences > Chemical sciences

Other information

Authenticus ID: 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.

Language: English

Type (Professor's evaluation): Scientific

No. of pages: 6