Restricted Rotation Involving the Tetrahedral Carbon. II. 2-Substituted 4,6,8-Trimethylazulenes

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概要

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• 1-(1-Hydroxyethyl)-4,6,8-trimethylazulene (<B>3</B>) was prepared by the lithium aluminum hydride reduction of 1-acetyl-4,6,8-trimethylazulene, and by the reaction of methylmagnesium iodide with 1-formyl-4,6,8-trimethylazulene. <B>3</B> showed various melting points according to its crystallization conditions and the reaction solvent. Their IR spectra both in solid states and in solutions, the NMR spectra at various temperatures, and the results of X-ray diffraction studies led to a conclusion that this phenomenon is attributable to polymorphism. From the temperature dependence of the NMR spectra of the <I>t</I>-butyl protons of 1-<I>t</I>-butyl-4,6,8-trimethylazulene, the internal rotation around the C<SUB>Bu</SUB>–C<SUB>azulene</SUB> was concluded to be slow only at the lower temperature.

• 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

• Nakamura Nobuo

  Department Of Cardiology Seiyu Memorial Hospital

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