Geminal Bond Participation in the Electrocyclic Reactions: Torquoselectivities of Silyl and Trimethylsilyl Derivatives of Cyclobutene, Iminocyclobutene, and Cyclobutenone

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  • Hirotaka Ikeda
    Department of Chemistry, Faculty of Engineering, Gifu University
  • Takayuki Kato
    Department of Chemistry, Faculty of Engineering, Gifu University
  • Satoshi Inagaki
    Department of Chemistry, Faculty of Engineering, Gifu University

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<jats:title>Abstract</jats:title> <jats:p>Analysis of the bond interactions at the transition state of the electrocyclic reaction of cyclobutene shows significant participation of the inward- and outward-rotating σ bonds geminal to the reacting centers. Electron-donating capabilities of the inward-rotating σ bonds are predicted to accelerate the reactions. The prediction of the torquoselectivities is confirmed by calculated preference of the inward rotations of the silyl and trimethylsilyl groups in cyclobutene, iminocyclobutene, and cyclobutenone.</jats:p>

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  • Chemistry Letters

    Chemistry Letters 30 (3), 270-271, 2001-03-01

    Oxford University Press (OUP)

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