Restricted rotation involving the tetrahedral carbon. XLIV. Atropisomers of 2,3-dichloro-9-(1-hydroxy-1-methylethyl)-triptycene and related compounds.
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概要
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Atropisomers of 2,3-dichloro-9-(1-hydroxy-1-methylethyl)triptycene were obtained as stable compounds at room temperature. The barrier to rotation (±<I>sc</I>→<I>ap</I>) was 34.0 kcal/mol at 153 °C. Other 9-(1-hydroxy-1-methylethyl)triptycenes carrying a substituent in the 1-position of the skeleton gave ±<I>sc</I> isomers only. Attempted isomerization of the ±<I>sc</I> forms failed because the free energy difference between the ±<I>sc</I> and <I>ap</I> forms is great due to the steric effect. ±<I>sc</I>-9-(1-Methoxy-1-methylethyl)-1,4-dimethyltriptycene was prepared in a hope that increasing the steric size of the hydroxyl group would help to produce an <I>ap</I>-isomer on heating. The <I>ap</I> isomer was detected but the population ratio <I>ap</I>⁄±<I>sc</I> was too small to isolate the <I>ap</I>.
- 公益社団法人 日本化学会の論文
著者
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Yamamoto Gaku
Department Of Chemistry Faculty Of Science 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 Nobuo
Department Of Cardiology Seiyu Memorial Hospital
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Tanaka Yoshiyuki
Department Of Biology Faculty Of Science Kobe University
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