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Volumn 47, Issue 37, 2006, Pages 6509-6511

Preparation and synthetic application of methyl β,β-difluoro-α-trimethylsilyloxyacrylate: a fluoride ion-promoted desilylative-defluorination route

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; BETA,BETA DIFLUORO ALPHA TRIMETHYLSILYLOXYACRYLATE; FLUORIDE; UNCLASSIFIED DRUG;

EID: 33746850550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.07.049     Document Type: Article
Times cited : (13)

References (15)
  • 3
    • 0010914582 scopus 로고
    • Intramolecular version: Both removable fluorine and trimethylsilyl group are involved in the same substrate. While there is another type of desilylative-defluorination where a substrate bearing a C-F bond does not involve a silyl group (intermolecular version):
    • Intramolecular version: Both removable fluorine and trimethylsilyl group are involved in the same substrate. While there is another type of desilylative-defluorination where a substrate bearing a C-F bond does not involve a silyl group (intermolecular version):. Zhang Y.F., Kirchmeier R.L., and Shreeve J.M. J. Fluorine Chem. 68 (1994) 287-292
    • (1994) J. Fluorine Chem. , vol.68 , pp. 287-292
    • Zhang, Y.F.1    Kirchmeier, R.L.2    Shreeve, J.M.3
  • 10
    • 33746847437 scopus 로고    scopus 로고
    • note
    • The use of KF (0.2 mol %) in THF was effective, but it required a rather higher temperature and a longer reaction time (50 °C for 10 h). The use of TBAF was useless for the purpose. The base provided mainly O-TMS trifluorolactate presumably due to the protonation of enolate intermediate from 7 with moisture involved in TBAF.
  • 11
    • 33746805173 scopus 로고    scopus 로고
    • note
    • 4
  • 12
    • 0034723340 scopus 로고    scopus 로고
    • 19F NMR: Some reactions of difluoroalkenes with nucleophiles:
    • 19F NMR: Some reactions of difluoroalkenes with nucleophiles:. Huang X.-H., He P.-Y., and Shi G.-Q. J. Org. Chem. 65 (2000) 627-629
    • (2000) J. Org. Chem. , vol.65 , pp. 627-629
    • Huang, X.-H.1    He, P.-Y.2    Shi, G.-Q.3
  • 15
    • 33746860476 scopus 로고    scopus 로고
    • note
    • Carbanion A is more stable than B.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.