Bulletin of the Korean Chemical Society

  • 제15권9호
  • /
  • Pages.729-732
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  • 1994
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Acid-Promoted Ring Cleavage Reactions of Silacyclohex-3-ene Derivatives

  • 발행 : 1994.09.20
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초록

The acid-promoted cleavage of the E-and Z-isomers of 1-phenyl-6-neopentyl-1,3,4-trimethyl-1-silacyclohe x-3-ene(II) under various conditions gave clean and nearly quantitative formation of the ring-opened 2,3,7,7-tetramethyl-5-(X)silyl-1-octene products (X=OMe, Cl, OH). The possible mechanism for the formation of the ring-opened products was suggested that the initial protonation of II at C-4 would give a carbocation oriented so that they are ${\beta}$ to the silicon atom, and the subsequent nucleophilic attack at silicon would give rise to the observed products (VI, VII, VIII).

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참고문헌

  1. J. Chem. Soc. Chem Commun. Eaborn, C.
  2. Sythesis Chan, T. H.;Fleming, I.
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  4. Organometallics v.2 Jones, P. R.;Pierce, R. A.;Cheng, H. B.
  5. Stereospecific Synthesis of Diastereomers via the Acid-Promoted Cleavage Reactions of 2-Silanorborn-5-ene Derivatives Lee, M. E.;Jun, H.;Kim, C. H.
  6. J. Am. Chem. Soc. v.99 Jones, P. R.;Lim, T. F. O.
  7. Organometallics v.2 Jones, P. R.;Lee, M. E.;Lin L. T.
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  11. J. Am. Chem. Soc. v.110 Lambert, J. B.;Schulz, W. J. Jr.;McConnell, J. A.;Schiff, W.
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  13. J. Am. Chem. Soc. v.110 Lambert, J. B.;Schiff, W.
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피인용 문헌

  1. Hosomi–Sakurai reactions of silacyclic allyl silanes vol.2006, pp.22, 2006, https://doi.org/10.1039/b602642g
  2. Hosomi–Sakurai reactions of silacyclohexenes vol.5, pp.17, 1994, https://doi.org/10.1039/b709318g