Reactivities of stable rotamers. XVIII Reactions of 9-[2-(1-hydroxyethyl)-1-naphthyl]fluorene rotamers with sulfuric acid and thionyl chloride.
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概要
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Treatment of the title compound with 70% sulfuric acid in 1,2-dimethoxyethane caused cyclization for the <I>ap</I> isomer, whereas it did dehydration to produce a vinyl compound smoothly for the <I>sp</I>. The same treatment with 10% sulfuric acid in 1,2-dimethoxyethane afforded the corresponding vinyl compounds from both rotamers. Treatment of the alcohol with thionyl chloride afforded the corresponding chloride in the case of the <I>sp</I>-alcohol, while it gave the <I>sp</I>-vinyl compound in addition to the <I>ap</I>-chloride in the case of the <I>ap</I>-alcohol. The change in solvents in the reaction of the <I>ap</I> form caused the change in the ratio of the olefin vs. the chloride: The polar solvents enhance the rates of formation of the chloride. Introduction of three deuteriums to the methyl group of the <I>ap</I>-form of the title compound suppressed the formation of the olefin to some extent. The results are explained on the grounds of steric effects in the ion-pair formation from the chlorosulfites and the contribution of the C–H stretching in the transition state of the elimination.
- 公益社団法人 日本化学会の論文
著者
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Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
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Nakamura Nobuo
Department Of Cardiology Seiyu Memorial Hospital
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Moriyama Kazuhiro
Department of Chemistry, Faculty of Science, The University of Tokyo
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Tsukahara Jiro
Department of Chemistry, Faculty of Science, The University of Tokyo
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