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Volumn 78, Issue 8, 2005, Pages 1520-1527

Substituent-control of two modes of intramolecular reactions of allyloxy-silyllithiums and propargyloxy-silyllithiums

Author keywords

[No Author keywords available]

Indexed keywords

OLEFINS; REACTION KINETICS; SUBSTITUTION REACTIONS;

EID: 23844555849     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.78.1520     Document Type: Article
Times cited : (3)

References (57)
  • 1
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    • (1986) Chem. Rev. , vol.86 , pp. 885
    • Nakai, T.1    Mikami, K.2
  • 17
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    • ed by Z. Rappoport and Y. Apeloig, John-Wiley & Sons, Chichester
    • c) J. Belzner and U. Dehnert, "The Chemistry of Organic Silicon Compounds," ed by Z. Rappoport and Y. Apeloig, John-Wiley & Sons, Chichester (1998), Vol. 2, pp. 779-826.
    • (1998) The Chemistry of Organic Silicon Compounds , vol.2 , pp. 779-826
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  • 22
    • 33645358112 scopus 로고    scopus 로고
    • note
    • The terms "prim-, sec-, and teri-allyloxy" mean that the allylic carbon is primary, secondary, and tertiary, respectively.
  • 24
    • 33645341470 scopus 로고    scopus 로고
    • note
    • 5b,7 the use of this term does not seem to be appropriate since the term has been used almost only for the cyclopropanation reactions of olefins with carbenes or carbenoids.
  • 25
    • 33645376219 scopus 로고    scopus 로고
    • note
    • Part of the results has already been presented in Refs. 5b and 7.
  • 26
    • 0001469016 scopus 로고    scopus 로고
    • The sec-allyl alcohols and sec-propargyl alcohols were prepared according to the procedures in the literature: a) S. E. Denmark and S. P. O'Connor, J. Org. Chem., 62, 584 (1997).
    • (1997) J. Org. Chem. , vol.62 , pp. 584
    • Denmark, S.E.1    O'Connor, S.P.2
  • 35
    • 0026675211 scopus 로고
    • Recent examples of 1,3-cycloelimination: a) A. Krief and M. Hobe, Tetrahedron Lett., 33, 6527 (1992).
    • (1992) Tetrahedron Lett. , vol.33 , pp. 6527
    • Krief, A.1    Hobe, M.2
  • 41
    • 33645369182 scopus 로고    scopus 로고
    • note
    • Although silyllithium compounds undergo substitution reactions with organic halides, 1,2- and 1,4-additions to carbonyl compounds, and allylic substitution reactions with allylic halides, the addition of silyllithiums to olefins has been scarcely reported, see Refs. 3 and 17.
  • 48
    • 0012364587 scopus 로고
    • ed by L. S. Liebeskind, JAI Press
    • For a review of other silylmetallations: K. Oshima, "Advances in Metal-Organic Chemistry," ed by L. S. Liebeskind, JAI Press (1991), Vol. 2, pp. 101-141.
    • (1991) Advances in Metal-Organic Chemistry , vol.2 , pp. 101-141
    • Oshima, K.1
  • 52
    • 33645354851 scopus 로고    scopus 로고
    • note
    • Two molar amounts of MeLi were required to consume the silylstannanes completely.
  • 53
    • 0001661548 scopus 로고    scopus 로고
    • and see also Ref. 1a
    • For an example of the [2,3]-Wittig rearrangement of propargyl alcohol derivatives: S. Manabe, Chem. Commun., 1997, 737, and see also Ref. 1a.
    • (1997) Chem. Commun. , pp. 737
    • Manabe, S.1
  • 54
    • 0025019481 scopus 로고
    • For examples of the 4-exo-dig cyclization of acetylenic alkyllithiums: a) W. F. Bailey and T. V. Ovaska, Tetrahedron Lett., 31, 627 (1990).
    • (1990) Tetrahedron Lett. , vol.31 , pp. 627
    • Bailey, W.F.1    Ovaska, T.V.2
  • 56
    • 0000840216 scopus 로고    scopus 로고
    • A similar type of oxasilacyclobutenes was isolated as products of palladium-catalyzed intramolecular bis-silylation of propargylic alcohols: M. Suginome, A. Matsumoto, and Y. Ito, J. Org. Chem., 61, 4884 (1996).
    • (1996) J. Org. Chem. , vol.61 , pp. 4884
    • Suginome, M.1    Matsumoto, A.2    Ito, Y.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.