The Stereochemistry of the Addition of Trimethylaluminum to Decalones and Methyl-substituted Cyclohexanones
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概要
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The addition to the methyl-substituted 4-<I>t</I>-butylcyclohexanone was studied, providing that the β-axial methyl and α-axial methyl groups hindered the axial and equatorial attacks respectively. The results obtained with fused-ring system ketones (four decalones) were explained by considering the similar stereochemical influence of 2-and 3-methylene substituents as corresponding methyl substituents. A rapid conformation equilibrium was also considered for <I>cis</I>-decalones. In addition, the axial attack, especially at a molar ratio of two or more, was found to be hindered by the α-equatorial methyl group. This hindrance was explained by assuming the half-chair form of the cyclohexanone ring in the transition state.
- 公益社団法人 日本化学会の論文
著者
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SUZUKI Toshimitsu
Department of Chemical Engineering
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Kobayashi Toshiaki
Department Of Applied Physics And Chemistry The University Of Electro-communications
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Takegami Yoshinobu
Department of Fuel Chemistry Faculty of Engineering Kyoto University
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Kobayashi Toshiaki
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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Kawasaki Yuzo
Department of Hydrocarbon Chemistry, Faculty of Engineering, Kyoto University
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