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

• Oki Michinori

  Department Of Chemistry Faculty Of Science Okawama University Of Science

• Nakamura Nobuo

  Department Of Cardiology Seiyu Memorial Hospital

• Moriyama Kazuhiro

  Department of Chemistry, Faculty of Science, The University of Tokyo

• Tsukahara Jiro

  Department of Chemistry, Faculty of Science, The University of Tokyo

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