Noriceane (tetracyclo(5.3.1.02,6.04,9)undecane) and 3,5-dehydronoriceane (pentacyclo(5.3.1.02,6.03,5.04,9)undecane).

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概要

• 論文の詳細を見る

• Heating a mixture <I>endo</I>, <I>exo</I>- and <I>endo</I>, <I>endo</I>-2,4-dibromohomoadamantanes at 180 °C in hexamethylphosphoric triamide (HMPT) brings about a novel skeletal rearrangement with concomitant dehydrobromination to give tricyclo[5.3.1.0<SUP>4,9</SUP>]undeca-2,5-diene (<B>5</B>) in 88% yield. Direct photoexcitation of <B>5</B> in diethyl ether induces an intramolecular [2+2] cycloaddition to produce 3,5-dehydronoriceane (<B>2</B>). The bicyclo[2.1.0]pentane moiety constrained in the cage structure of <B>2</B> shows almost the same <SUP>13</SUP>C–H coupling constants as those of bicyclo[2.1.0]pentane itself. Finally hydrogenation of <B>2</B> over PtO<SUB>2</SUB> easily proceeds to afford noriceane, which is named after the structure of iceane.

• 公益社団法人 日本化学会の論文

著者

• Katsushima Takeo

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

• Yamaguchi Ryohei

  Department of Applied Chemistry, Faculty of Engineering, Yokohama National University

• Kawanisi Mituyosi

  Department of Industrial Chemistry, Faculty of Engineering Kyoto University

関連論文

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