Restricted Rotation Involving the Tetrahedral Carbon. I. Some Diels-Alder Adducts Derived from 9-Substituted Anthracenes

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概要

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• 9-<I>t</I>-Butylanthracene was treated with dimethyl acetylenedicarboxylate and benzoquinone to give Diels-Alder adducts. The NMR spectra of these adducts suggest that the internal rotation about the C<SUB>1</SUB>–C<SUB>Bu</SUB> bond is not taking place on the NMR time scale. On the other hand, a Diels-Alder adduct prepared from 9-isopropylanthracene and dimethyl acetylenedicarboxylate shows the coalescence phenomenon of the NMR signals when the temperature is raised. The possibility of optical resolution due to hindered rotation about the <I>sp</I><SUP>3</SUP>–<I>sp</I><SUP>3</SUP> carbon bond is pointed out.

• 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

• Suda Minoru

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

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