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Volumn 3, Issue 9, 2001, Pages 1379-1381

cis-vinylphosphonates and 1,3-butadienylphosphonates by zirconation of 1-alkynylphosphonates

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ARTICLE;

EID: 0002815779     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0157454     Document Type: Article
Times cited : (51)

References (41)
  • 10
    • 0026528113 scopus 로고
    • Selected recent reactions of vinylphosphonates include the following. Aziridination
    • For a recent review, see: (a) Minami I, T.; Motoyoshiya, J. Synthesis 1992, 333. Selected recent reactions of vinylphosphonates include the following. Aziridination:
    • (1992) Synthesis , pp. 333
    • Minami, I.T.1    Motoyoshiya, J.2
  • 11
  • 20
  • 22
    • 0000443799 scopus 로고
    • Paquette, L. A., Ed.; Pergamon Press: New York
    • (b) Negishi, E. In Comprehensive Organic Synthesis; Paquette, L. A., Ed.; Pergamon Press: New York, 1991; Vol. 5, p 1163.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 1163
    • Negishi, E.1
  • 24
    • 3543010016 scopus 로고
    • (a) L'vova, S. D.; Kozlov, Yu, P.; Gunar, V. I. J. Gen. Chem. USSR (Engl. Transl.) 1977, 47, 1153; Zh. Obshch. Khim. 1977, 47, 1251.
    • (1977) Zh. Obshch. Khim. , vol.47 , pp. 1251
  • 30
    • 0009520294 scopus 로고
    • All 1-alkynylphosphonates were prepared by reaction of the corresponding lithium acetylide with diethyl chlorophosphates: (a) Poss, A. J.; Belter, R. K. J. Org. Chem. 1987, 52, 4810.
    • (1987) J. Org. Chem. , vol.52 , pp. 4810
    • Poss, A.J.1    Belter, R.K.2
  • 36
    • 0042621555 scopus 로고    scopus 로고
    • note
    • To 1 mmol (0.292 g) of zirconocene dichloride dissolved in 5 mL of dry THF was added 2 mmol (1.25 mL of n-BuLi 1.6 M in hexane) dropwise at -78 °C. The mixture was stirred for 3 h, then 0.9 mmol of 1-alkynylphosphonate was added, and the mixture was slowly warmed to 25 °C and stirred overnight. The mixture was worked up with dilute aqueous HCl, and the vinylphosphonate was extracted in ether and separated on a silica gel column (80% petroleum ether: 20% ethyl acetate).


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