메뉴 건너뛰기




Volumn 68, Issue 20, 2003, Pages 7800-7805

1-Trifluoromethylvinylsilane as a CF2=C--CH 2+ synthon: Synthesis of functionalized 1,1-difluoro-1-alkenes via isolable 2,2-difluorovinylsilanes

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHILES;

EID: 0141654012     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034718j     Document Type: Article
Times cited : (105)

References (73)
  • 4
    • 0141806914 scopus 로고
    • ACS Symp. Ser. No. 456; Welch, J. T., Ed.; American Chemical Society: Washington, DC
    • (d) Selective Fluorination in Organic and Bioorganic Chemistry; ACS Symp. Ser. No. 456; Welch, J. T., Ed.; American Chemical Society: Washington, DC, 1991.
    • (1991) Selective Fluorination in Organic and Bioorganic Chemistry
  • 5
    • 0141695412 scopus 로고    scopus 로고
    • ACS Symp. Ser. No. 639; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC
    • (e) Biomedical Frontiers of Fluorine Chemistry; ACS Symp. Ser. No. 639; Ojima, I., McCarthy, J. R., Welch, J. T., Eds.; American Chemical Society: Washington, DC, 1996.
    • (1996) Biomedical Frontiers of Fluorine Chemistry
  • 13
    • 0001096111 scopus 로고    scopus 로고
    • and references therein
    • Ichikawa, J. J. Fluorine Chem. 2000, 105, 257 and references therein.
    • (2000) J. Fluorine Chem. , vol.105 , pp. 257
    • Ichikawa, J.1
  • 38
    • 0141472158 scopus 로고    scopus 로고
    • note
    • 5d
  • 50
    • 0001091845 scopus 로고
    • The favorable effect of an α-silyl group in α,β -unsaturated enones on the Michael reaction is well documented. Stork, G.; Ganem, B. J. Am. Chem. Soc. 1973, 95, 6152.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 6152
    • Stork, G.1    Ganem, B.2
  • 54
    • 0035844666 scopus 로고    scopus 로고
    • The Grignard reagent was prepared from 2-bromo-3,3,3-trifluoro-1-propene in the presence of an electrophile. Jiang, B.; Wang, Q.-F.; Yang, C.-G.; Xu, M. Tetrahedron Lett. 2001, 42, 4083.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 4083
    • Jiang, B.1    Wang, Q.-F.2    Yang, C.-G.3    Xu, M.4
  • 57
    • 0002701930 scopus 로고
    • Trost, B. M., Ed.; Pergamon: Oxford, UK
    • (b) Lee, V. J. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: Oxford, UK, 1991; Vol. 4, p 69.
    • (1991) Comprehensive Organic Synthesis , vol.4 , pp. 69
    • Lee, V.J.1
  • 59
    • 0000149398 scopus 로고
    • The replacement of the vinylic fluorines in 9b by n-BuLi readily proceeded at -45 °C to give 5-fluoro-6-dimethylphenylsilyl-5-undecene in 93% yield (E:Z = 12:88). The same reaction of 1,1-difluoro-2-phenyl-1-hexane with n-BuLi occurred at -45 °C to afford 5-fluoro-6-phenyl-5-decene in 95% yield (E:Z = 69:31). These results reveal that the effect of silicon works as favorably as that of the phenyl group in the substitution of the vinylic fluorines. The stereochemistry of the E and Z isomers was determined by NOESY spectroscopy. See also: (a) Martin, S.; Sauvêtre, R.; Normant, J.-F. Tetrahedron Lett. 1983, 24, 5615.
    • (1983) Tetrahedron Lett. , vol.24 , pp. 5615
    • Martin, S.1    Sauvêtre, R.2    Normant, J.-F.3
  • 62
    • 0141472152 scopus 로고    scopus 로고
    • note
    • 4NF (1.0 M) contained water (10 vol %).
  • 73
    • 0000059554 scopus 로고    scopus 로고
    • and references therein
    • For reports on the utility of 3,3-difluoroallylic alcohols, see: Patel, S. T.; Percy, J. M.; Wilkens, R. D. J. Org. Chem. 1996, 61, 166 and references therein.
    • (1996) J. Org. Chem. , vol.61 , pp. 166
    • Patel, S.T.1    Percy, J.M.2    Wilkens, R.D.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.