Chemistry of dienyl anions. III. Crystalline bis(2,4-pentadienyl)metal compounds of Be and Zn. Terminally .SIGMA.-bonded structure and fluxional 1,5-rearrangement.

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• A series of bis(dienyl)beryllium and bis(dienyl)zinc compounds were prepared by metal exchange reaction from seven different dienyl anions and were isolated as crystals of TMEDA complexes. Bis(dienyl)beryllium compounds of open chain structure obtained from pentadienyl, 2-methylpentadienyl, and 3-methylpentadienyl anions assume the terminally σ-bonded (<I>E</I>)-2,4-pentadienyl structure in solution as evidenced by <SUP>1</SUP>H-NMR and <SUP>13</SUP>C-NMR spectroscopies. Hydrolysis of these compounds gave 1,4-dienes regioselectively. The corresponding bis(dienyl)zinc compounds exist as a (<I>Z</I>), (<I>E</I>) mixture of teminally σ-bonded structures. An X-ray analysis of pentadienylzinc chloride·TMEDA complex showed that it had terminally σ-bonded (<I>E</I>)-2,4-pentadienyl structure with <I>s</I>-<I>trans</I> conformation. Steric effect of two methyl substituents in bis(2,4-dimethylpentadienyl)zinc induces the (<I>Z</I>) configuration which leads to the fluxional behavior by rapid 1,5-rearrangement above −80 °C.

• 公益社団法人 日本化学会の論文

著者

• Kai Yasushi

  Department Of Applied Chemistry Faculty Of Engineering Osaka University

• Yasuda Hajime

  Department Of Applied Chemistry Faculty Of Engineering Hiroshima University

• Kasai Nobutami

  Department Of Applied Biological Science Tokyo University Of Science

• Yasuoka Noritake

  Department Of Life Science Faculty Of Science Himeji Institute Of Technology

• Nakamura Akira

  Department Oc Macromolecular Science Faculty Of Science Osaka University

• Ohnuma Yasuo

  Department of Macromolecular Science, Faculty of Science, Osaka University

• Yasuoka Noritake

  Department of Applied Chemistry, Faculty of Engineering, Osaka University

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