Restricted rotation involving the tetrahedral carbon. XLIII. Buttressing effect on rotational barriers in bromine-substituted 9-(2-methoxy-4,6-dimethylphenyl)fluorenes.
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概要
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9-(2-Methoxy-4,6-dimethylphenyl)fluorenes carrying one or two bromo groups on the phenyl ring were prepared and the buttressing effect on the rotational barrier about the C<SUB>9</SUB>–C<SUB>ph</SUB> bond were investigated. The free energies of activation for rotation were 26.5, 25.9, and 27.2 kcal/mol at 56 °C for 3-bromo, 5-bromo, and 3,5-dibromo compounds, respectively. The buttressing effect was enhanced when the bromo group was next to the methoxyl group relative to that given to the methyl group. The results were attributed to the fact that a methoxyl group, which gives its steric effect by the oxygen atom in the normal cases, has to take conformations, not coplanar with the phenyl ring, caused by the presence of the bromo group.
- 公益社団法人 日本化学会の論文
著者
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Aoki Masahiro
Department of Cell Biology, National Institute for Basic Biology
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Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
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Nakamura Mikio
Department Of Anatomy Jikei-kai School Of Medicine
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Aoki Masahiro
Department of Chemistry, Faculty of Science, The University of Tokyo
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