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Volumn 41, Issue 16, 1985, Pages 3257-3268

Cleavage of vinyl carbon-silicon bond with tetrabutylammonium fluoride

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Indexed keywords


EID: 0043162088     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(01)96677-3     Document Type: Article
Times cited : (60)

References (35)
  • 10
    • 84918078758 scopus 로고    scopus 로고
    • 4NF in THF-DMSO (1:1) at 80°C for 30 min gave decyldimethylsilanol in 70% yield, whereas decyldimethylvinylsilane was recovered completely unchanged under the same reaction conditions.
  • 15
    • 84918078757 scopus 로고    scopus 로고
    • The cleavage of these vinylsilanes gave irreproducible results and various yields of desilylated products were obtained.
  • 16
    • 84918078756 scopus 로고    scopus 로고
    • The hydrogen bonding as shown in 49 explains the facile cleavage of 29 and 31 as suggested by Chan, but we assume the intramolecular participation of 50 to account for the reactivities of 37 and 45. Remarkably, 11 (Table 1) and 2-allyl-1-dimethylphenylsilyl-1-dodecene also react with tetrabutyl-ammonium fluoride at room temperature to give excellent yields of the corresponding hydrocarbons. This is ascribed to the acceleration given in 51.
  • 24
    • 84918078755 scopus 로고    scopus 로고
    • Low yield of enal was ascribed to the formation of many byproducts based on retro-Aldol reaction of the intermediary β-hydroxy aldehyde. In fact, heptanal and pentanal were detected in the reaction mixture by glpc.
  • 25
    • 84918078754 scopus 로고    scopus 로고
    • T.K. Sarkar and N.H. Andersen, Tetrahedron Lett., 1978, 3513
  • 26
    • 84918078753 scopus 로고    scopus 로고
    • A. Hosomi, A. Shirahata and H. Sakurai, Chem. Lett., 1978, 901
  • 29
    • 84918078752 scopus 로고    scopus 로고
    • I. Fleming and F. Roessler, Chem. Commun., 1980, 276
  • 30
    • 84918078751 scopus 로고    scopus 로고
    • I. Fleming, T.W. Newton, and F. Roessler, J. Chem. Soc. Perkin Trans. I, 1981, 2527.
  • 32
    • 0009934992 scopus 로고
    • Prepared by hydroalumination of 1-octyne according to Utimoto's method and successive treatment with iodine
    • (1976) J. Org. Chem. , vol.41 , pp. 2215
    • Uchida1    Utimoto2    Nozaki3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.