Layered compounds. LIII. Unique skeletal rearrangement of multilayered [2.2]paracyclophanes.

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概要

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• Skeletal rearrangements of multilayered [2.2]paracyclophanes to [2.2]metaparacyclophanes with several Friedel-Crafts acids have been studied. Two types of rearrangements depending on the catalyst were observed. Treatment of triple-layered paracyclophane(<B>8</B>) with AlCl<SUB>3</SUB>–HCl gave mainly triple-layered metaparacyclophane(<B>9</B>), which was derived by migration of one of the ethylene bridges attached to the outer benzene rings. Treatment of <B>8</B> with mild protonic acids such as SnCl<SUB>4</SUB>–HCl, TiCl<SUB>4</SUB>–HCl, <I>etc</I>. afforded two kinds of metaparacyclophanes <B>10</B> and <B>11</B> in high yields, which arose from double migration of the two ethylene bridges attached to the inner benzene ring. Such a double migration of substitutents was also observed in the case of tertamethyl[2.2]paracyclophane and quadruple-layered one. The structures of products were determined by means of NMR spectra, alternative syntheses, and X-ray analyses. The mechanism of the rearrangements is discussed in view of protonation experiment.

• 公益社団法人 日本化学会の論文

著者

• Sakata Yoshiteru

  The Institute Of Science And Industrial Research Osaka University

• Misumi Soichi

  The Institute Of Scientific And Industrial Research Osaka University

• Otsubo Tetsuo

  The Institute of Scientific and Industrial Research, Osaka University

• Koizumi Yosuke

  The Institute of Scientific and Industrial Research, Osaka University

• Horita Hisanori

  The Institute of Scientific and Industrial Research, Osaka University

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