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Volumn , Issue 14, 1996, Pages 1615-1616

A DAST-free route to aryl(difluoromethyl)phosphonic esters

Author keywords

[No Author keywords available]

Indexed keywords

BENZOQUINONE; CERIUM; PHENOL; PHOSPHONIC ACID ESTER; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 0029890016     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/cc9960001615     Document Type: Article
Times cited : (16)

References (20)
  • 2
    • 33751155275 scopus 로고
    • and references cited therein
    • For recent publications, see S. Halazy, A. Ehrhard, A. Eggenspiller, V. Bergés-Gross and C. Danzin, Tetrahedron, 1996, 52, 177; D. B. Berkowitz and D. G. Sloss, J. Org. Chem., 1995, 60, 7047 and references cited therein.
    • (1995) J. Org. Chem. , vol.60 , pp. 7047
    • Berkowitz, D.B.1    Sloss, D.G.2
  • 4
    • 0028206694 scopus 로고
    • T. R. Burke, M. S. Smyth, A. Otaka and P. P. Roller, Tetrahedron Lett., 1993, 34, 4125; T. R. Burke and M. S. Smyth, Tetrahedron Lett., 1994, 35, 551.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 551
    • Burke, T.R.1    Smyth, M.S.2
  • 7
    • 0027318389 scopus 로고
    • A Wyeth group described an alternative route that relies on a DAST transformation; J. Wrobel and A. Dietrich, Tetrahedron Lett., 1993, 34 3543. Burton and Qiu have described a direct route based on organocadmium chemistry; D. J. Burton and W. Qiu, Tetrahedron Lett., 1996, 37, 2745.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3543
    • Wrobel, J.1    Dietrich, A.2
  • 8
    • 0343526163 scopus 로고    scopus 로고
    • A Wyeth group described an alternative route that relies on a DAST transformation; J. Wrobel and A. Dietrich, Tetrahedron Lett., 1993, 34 3543. Burton and Qiu have described a direct route based on organocadmium chemistry; D. J. Burton and W. Qiu, Tetrahedron Lett., 1996, 37, 2745.
    • (1996) Tetrahedron Lett. , vol.37 , pp. 2745
    • Burton, D.J.1    Qiu, W.2
  • 9
    • 0029924009 scopus 로고    scopus 로고
    • The DAST reaction is prone to a sudden dramatic but unpredictable exotherm, particularly on gram-scales, T. R. Burke, personal communication to J. M. P. Invariably, a large excess of the reagent is required. In a recent publication, no fewer than 15 equiv. were employed to fluorinate a ketophosphonate. See D. Solas, R. L. Hale and D. V. Patel, J. Org. Chem., 1996, 61, 1537.
    • (1996) J. Org. Chem. , vol.61 , pp. 1537
    • Solas, D.1    Hale, R.L.2    Patel, D.V.3
  • 11
    • 8944230408 scopus 로고
    • The starting material is expensive but has been prepared on a multigram scale using an electrochemical procedure described by M. Azadiardakani and T. W. Wallace, J. Chem. Ed., 1986, 63, 822.
    • (1986) J. Chem. Ed. , vol.63 , pp. 822
    • Azadiardakani, M.1    Wallace, T.W.2
  • 12
    • 0002524054 scopus 로고
    • T. P. Lequeux and J. M. Percy, Synlett., 1995, 361; T. P. Lequeux and J. M. Percy, J. Chem Soc., Chem. Commun., 1995, 2111. The addition of carbon nucleophiles to related systems has been studied in some detail; P. Wipf and Y. Kim, J. Am. Chem. Soc., 1994, 116, 11678.
    • (1995) Synlett. , pp. 361
    • Lequeux, T.P.1    Percy, J.M.2
  • 13
    • 37049089086 scopus 로고
    • T. P. Lequeux and J. M. Percy, Synlett., 1995, 361; T. P. Lequeux and J. M. Percy, J. Chem Soc., Chem. Commun., 1995, 2111. The addition of carbon nucleophiles to related systems has been studied in some detail; P. Wipf and Y. Kim, J. Am. Chem. Soc., 1994, 116, 11678.
    • (1995) J. Chem Soc., Chem. Commun. , pp. 2111
    • Lequeux, T.P.1    Percy, J.M.2
  • 14
    • 0000630657 scopus 로고
    • T. P. Lequeux and J. M. Percy, Synlett., 1995, 361; T. P. Lequeux and J. M. Percy, J. Chem Soc., Chem. Commun., 1995, 2111. The addition of carbon nucleophiles to related systems has been studied in some detail; P. Wipf and Y. Kim, J. Am. Chem. Soc., 1994, 116, 11678.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11678
    • Wipf, P.1    Kim, Y.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.