The Nickel-catalyzed Cyclodimerization of Butadiene. The Synthesis of 2-Methylenevinylcyclopentane and the Isomerization of 1,3,7-Octatriene

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概要

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• A catalyst system of NiX<SUB>2</SUB>(R<SUB>3</SUB>P)<SUB>2</SUB>–NaBH<SUB>4</SUB> or –R′ONa (X=halogen, R and R′=alkyl) was found to yield 2-methylenevinylcyclopentane (MVCP) and <I>n</I>-octatrienes (OT), depending on the amount of NaBH<SUB>4</SUB> or R′ONa, which act as a reducing agent for the nickel halide. Less than an equimolar amount of the reducing agent provides a catalyst for MVCP, whereas an excess amount provides that for <I>n</I>-octatrienes. In the latter case, the nickel halide is reduced to zero-valent nickel, which then reacts with hydrogen halide to give a catalyst for MVCP again. The catalyst (<2:1 ratio of reducing agent: Ni) was also effective in the isomerization of 1,3,7-octatriene to MVP.

• 公益社団法人 日本化学会の論文

著者

• Furukawa Junji

  Department Of Applied Chemistry Aichi Institute Of Technology

• Yoshikawa Susumu

  Depart. Organic Materials Osaka National Research Institute

• Yamamoto Kazuyoshi

  Department Of Chemical Engineering

• Kiji Jitsuo

  Department of Chemistry Faculty of Science Osaka University

• Yamamoto Kazuyoshi

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

• Mitani Shin-ichi

  Department of Synthetic Chemistry, Faculty of Engineering, Kyoto University

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