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Volumn 558, Issue 1-2, 1998, Pages 227-230

Migration of aryl groups from silicon to carbon in α,β-epoxysilanes. A new model for hypervalent silicon study

Author keywords

Aryl group migaration; Hypervalent Si species; , Epoxysilanes

Indexed keywords


EID: 0032523473     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(97)00677-3     Document Type: Article
Times cited : (7)

References (44)
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    • (a) For reviews, see: in: G.L. Larson (Ed.) Jai Press, Greenwich
    • For reviews, see: (a) P.F. Hudrlik, A.H. Hudrlik, in: G.L. Larson (Ed.), Advances in Silicon Chemistry, vol. 2, Jai Press, Greenwich, 1993, p. 1;
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    • (b) in: S. Patai, Z. Rappoport (Eds.) John Wiley, Chichester
    • (b) A.R. Bassindale, P.G. Taylor, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Organosilicon Compounds, John Wiley, Chichester, 1989, p. 893-964. P. Jankowski, S. Marczak, M. Masnyk, J. Wicha, J. Organomet. Chem. 403 (1991) 49-62.
    • (1989) The Chemistry of Organosilicon Compounds , pp. 893-964
    • Bassindale, A.R.1    Taylor, P.G.2
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    • (b)
    • (b) A.R. Bassindale, P.G. Taylor, in: S. Patai, Z. Rappoport (Eds.), The Chemistry of Organosilicon Compounds, John Wiley, Chichester, 1989, p. 893-964. P. Jankowski, S. Marczak, M. Masnyk, J. Wicha, J. Organomet. Chem. 403 (1991) 49-62.
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    • Jankowski, P.1    Marczak, S.2    Masnyk, M.3    Wicha, J.4
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    • (a) An alkyl group migration has been noted in a silacyclobutane
    • (a) An alkyl group migration has been noted in a silacyclobutane, K. Matsamuto, Y. Takeyama, K. Oshima, K. Utimoto, Tetrahedron Lett. 32 (1991) 4545-4548;
    • (1991) Tetrahedron Lett. , vol.32 , pp. 4545-4548
    • Matsamuto, K.1    Takeyama, Y.2    Oshima, K.3    Utimoto, K.4
  • 24
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    • (b) For an example of acid-catalysed migration of the phenyl group from silicon to carbon in α,β-epoxysilanes, see
    • (b) For an example of acid-catalysed migration of the phenyl group from silicon to carbon in α,β-epoxysilanes, see: I. Fleming, T.W. Newton, J. Chem Soc. Perkin Trans. 1 (1984) 119-123.
    • (1984) J. Chem Soc. Perkin Trans. , vol.1 , pp. 119-123
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    • A Chiracel® OD-H analytical column, 0.46(I.D.)×25 cm with a precolumn 0.46×5 cm of Daicel Chemical Industries, Tokyo, Japan, has been used
    • A Chiracel® OD-H analytical column, 0.46(I.D.)×25 cm with a precolumn 0.46×5 cm of Daicel Chemical Industries, Tokyo, Japan, has been used.
  • 29
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    • (b) For a review on non-racemic glycidols, see
    • (b) For a review on non-racemic glycidols, see: R.M. Hanson, Chem. Rev. 91 (1991) 437-475.
    • (1991) Chem. Rev. , vol.91 , pp. 437-475
    • Hanson, R.M.1
  • 30
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    • 20=+38.7
    • 20=+38.7.
  • 36
    • 0001524306 scopus 로고
    • For examples of desilylation in acetonitrile, see: and ref. 11a
    • For examples of desilylation in acetonitrile, see: D.R. Boyd, G.A. Berchtold, J. Org. Chem. 44 (1979) 468-470 and ref. 11a.
    • (1979) J. Org. Chem. , vol.44 , pp. 468-470
    • Boyd, D.R.1    Berchtold, G.A.2
  • 37
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    • Origin of allyl alcohol is not quite clear at the present. Supplementary experiment has shown that γ-(triphenylsily)allyl alcohol undergoes partial desilylation under the applied conditions (in acetonitrile) although, in principle, vinylsilanes are desilylated much slower then epoxysilenes, see ref. 14
    • Origin of allyl alcohol is not quite clear at the present. Supplementary experiment has shown that γ-(triphenylsily)allyl alcohol undergoes partial desilylation under the applied conditions (in acetonitrile) although, in principle, vinylsilanes are desilylated much slower then epoxysilenes, see ref. 14.
  • 38
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    • 13C NMR spectra, while elemental composition was confirmed by combustion analysis
    • 13C NMR spectra, while elemental composition was confirmed by combustion analysis.
  • 41
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    • 20=-34.4
    • 20=-34.4.
  • 43
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    • (b) Please note that in transforming of 12 (R) into 14 (R) inversion of configuration around the silicon atom has occurred
    • (b) R.J.P. Corriu, G. Royo, Bull. Soc. Chim. Fr. (1972) 1497-1510. Please note that in transforming of 12 (R) into 14 (R) inversion of configuration around the silicon atom has occurred.
    • (1972) Bull. Soc. Chim. Fr. , pp. 1497-1510
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    • in: J.D. Morrison (Ed.) Academic Press, Orlando Chapter 8
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.