Reactivities of stable rotamers. IX. Ionizing reactions of 9-(2-bromomethyl-6-methylphenyl)fluorene rotamers.
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概要
- 論文の詳細を見る
Ionizing reactions of <I>ap</I>-9-(2-bromomethyl-6-methylphenyl)fluorene in ionizing solvents afforded 12-methyl-8,12b-dihydrobenz[<I>a</I>]aceanthrylene and its dehydrogenated compound, whereas the <I>sp</I> isomer remained intact. Forced ionization of the <I>sp</I> isomer with silver salts afforded products originated from the corresponding cation and either the anion of the salt or the solvent, whereas the <I>ap</I> isomer gave cyclized product under the same conditions, if the nucleophilicity of the solvent was poor. The reaction of the <I>sp</I> isomer was faster than the <I>ap</I> in nucleophilic solvents, whereas the reverse was true for poorly nucleophilic solvents. Solvolysis of the rotamers in formic acid yielded the corresponding formates, the <I>sp</I> isomer reacting faster than the <I>ap</I>. The results are discussed on the basis that the solvation shell in the <I>ap</I> form is completed by the participation of the fluorene ring whereas in the <I>sp</I> form the shell is completed by the solvent molecules.
- 公益社団法人 日本化学会の論文
著者
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Murata Shigeru
Department Of Basic Science Graduate School Of Arts And Sciences The University Of Tokyo
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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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Kanno Seiichiro
Department of Chemistry, Faculty of Science, The University of Tokyo
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Tanabe Yo
Department of Chemistry, Faculty of Science, The University of Tokyo
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Tanabe Yo
Department of Chemistry, Faculty of Science, Kyoto University
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