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Volumn 49, Issue 34, 2008, Pages 5059-5062

Preparation of halo enol phostones by reaction of acetylenic phosphonate monoesters with (bis-collidine)halo hexafluorophosphate

Author keywords

Bromo reagent; Electrophilic cyclization; Enol; Heterocyclic compound; Iodo reagent; Phospho lactone; Phosphorus compound

Indexed keywords

ACETIC ACID DERIVATIVE; COLLIDINE; ESTER DERIVATIVE; FLUOROPHOSPHATE;

EID: 46949094562     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.06.037     Document Type: Article
Times cited : (13)

References (27)
  • 2
    • 13744259692 scopus 로고    scopus 로고
    • The reactivity of conjugated acetylenic phosphonates has been reported:
    • The reactivity of conjugated acetylenic phosphonates has been reported:. Lahrache H., Robin S., and Rousseau G. Tetrahedron Lett. 46 (2005) 1635-1637
    • (2005) Tetrahedron Lett. , vol.46 , pp. 1635-1637
    • Lahrache, H.1    Robin, S.2    Rousseau, G.3
  • 15
    • 85083866311 scopus 로고    scopus 로고
    • Piomelli, D.; Beltramo, M. Patent WO 9824396, Chem. Abstract. 1998, 129, 62987.
    • Piomelli, D.; Beltramo, M. Patent WO 9824396, Chem. Abstract. 1998, 129, 62987.
  • 19
    • 85083866040 scopus 로고    scopus 로고
    • note
    • General procedure for the halo cyclizations: To a dichloromethane solution (5 mL) of (bis-collidine)halo hexafluorophosphate (0.36 mmol, 1.3 equiv) was added in the dark, in 2 h, a dichloromethane solution (3 mL) of monoester phosphonate (0.3 mmol). After 1 h at room temperature, the solvent was removed under vacuum and the residue was purified by liquid chromatography over silica gel (EtOAc).
  • 20
    • 85083869571 scopus 로고    scopus 로고
    • note
    • 13C NMR δ 146.2
  • 24
    • 85083866117 scopus 로고    scopus 로고
    • note
    • 31P NMR δ 30.9.
  • 25
    • 85083867002 scopus 로고    scopus 로고
    • note
    • Phostones 7-20 were found to be stable for several months at rt and several years at 0 °C. Phostones 19, 20 were stable after several days at pH 8.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.