Restricted rotation involving the tetrahedral carbon. L. Rotamer distributions and rotational barriers in some 9-(1-methoxyethyl)triptycene derivatives.

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概要

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• 1,4-Dimethyl-and 1,2,3,4-tetrahalo-9-(1-methoxyethyl)triptycenes (halogen=F, Cl, and Br) were synthesized by reactions of 9-(1-methoxyethyl)anthracene with appropriate benzynes. Rotamer distributions and rotational barriers about the bridgehead-to-substituent bond were studied by NMR spectroscopy. Rotamer distributions are governed mainly by the steric effect; the major rotamer is assigned to <I>sc</I><SUP>*</SUP>(<I>S</I><SUP>*</SUP>), the minor one to <I>ap</I>, and the third one found only in the tetrafluoro derivative to <I>sc</I><SUP>*</SUP>(<I>R</I><SUP>*</SUP>). Rotational barriers are 21–23 kcal mol<SUP>−1</SUP> which are slightly lower than those for the corresponding 9-isopropyltriptycenes.

• 公益社団法人 日本化学会の論文

著者

• Yamamoto Gaku

  Department Of Chemistry Faculty Of Science The University Of Tokyo

• Oki Michinori

  Department Of Chemistry Faculty Of Science Okawama University Of Science

• Tanaka Yoshiyuki

  Department Of Biology Faculty Of Science Kobe University

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