Reactivities of stable rotamers. XI. Rotamer distributions and some addition reactions to the carbonyl in 9-(2-(substituted carbonyl)-1-naphthyl)fluorene rotamers.
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概要
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Rotational isomers (<I>sp</I> and <I>ap</I>) of several 9-[2-(substituted carbonyl)-1-naphthyl]fluorenes where the substituent is methyl, phenyl, hydroxyl, methoxyl, 1-imidazolyl, or others have been obtained as stable entities. Barriers to rotation in these compounds were <I>ca.</I> 26.5 kcal for the process <I>sp</I>→<I>ap</I> but those for the reverse (<I>ap</I>→<I>sp</I>) were dependent on the substituent, ranging from 23.8 to 25.3 kcal/mol at 55 °C. The difference is reflected in the populations of rotamers: if the substituent is a hydroxyl, the <I>sp</I>/<I>ap</I> value becomes as large as <I>ca.</I> 20. The relative instability of the <I>ap</I> form was attributed to twisting of the carbonyl plane from that of naphthalene. Infrared spectra support the twisting. Addition reactions to the carbonyl occur smoothly in the <I>sp</I> conformation but they do not occur to a detectable extent in the <I>ap</I> conformation, if the substituent on the carbonyl is larger than hydrogen. The results are attributed to the steric effect of the fluorene ring.
- 公益社団法人 日本化学会の論文
著者
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Saito Ryo
Department Of Bioscience And Bioinformatics Faculty Of Computer Science And Systems Engineering Kyus
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Oki Michinori
Department Of Chemistry Faculty Of Science Okawama University Of Science
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Saito Ryo
Department of Chemistry, Faculty of Science, The University of Tokyo
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