Halogenation of 3,5-dehydronoriceane (pentacyclo(5.3.1.02,6.03,5.04,9)undecane. Front side attack on the bicyclo(2.1.0)pentane system by halonium ion and corner side attack by halogen radical.

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概要

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• Halogenations of 3,5-dehydronoriceane (<B>1</B>) in dichloromethane in the dark exclusively or predominantly give <I>endo</I>,<I>exo</I>-4,5-dihalotetracyclo[5.3.1.0<SUP>2,6</SUP>.0<SUP>3,9</SUP>]undecanes; these results provide a decisive evidence for the front side attack on the bicyclo[2.1.0]pentane system by halonium ion. On the other hand, the corner side attack on the bicyclo[2.1.0]pentane system by halogen radicals takes place in photohalogenations of <B>1</B>, which give <I>endo</I>,<I>endo</I>- and <I>endo</I>,<I>exo</I>-3,5-dihalonoriceanes. In addition, the halogenation of <B>1</B> in the dark is found to be sensitive to the solvent polarity and the ionic nature of the halogen used. Bromination of <B>1</B> in nonpolar solvents in the dark likely proceeds through intervention of the 1,3-bridged bromonium ion.

• 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

• Iemura Satoshi

  Department of Industrial Chemistry, Faculty of Engineering, Kyoto University

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