Diazomethane Addition to 5, 6-Disubstituted 2-Norbornene Derivatives

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  • Yanagida Yuji
    Department of Applied Chemistry, Faculty of Engineering, Osaka University
  • Yokota Toshio
    Department of Applied Chemistry, Faculty of Engineering, Osaka University
  • Nomura Masakatsu
    Department of Applied Chemistry, Faculty of Engineering, Osaka University
  • Kikkawa Shoichi
    Department of Applied Chemistry, Faculty of Engineering, Osaka University

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Other Title
  • 5,6-二置換 2-ノルボルネン類へのジアゾメタンの付加反応
  • ５，６‐二置換２‐ノルボルネン類へのジアゾメタンの付加反応

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Description

1, 3-Dipolar cycloaddition reaction of diazomethane to various 5, 6-disubstituted 2-norbornenes were investigated. All the adducts obtained were 1-pyrazoline derivatives. In the reaction of trans-5, 6-dicyano(or dicarbomethoxy)-2-norbornene, two isomers were isolated and the structures were determined by NMR analysis.<BR>Kinetic study in diethyl ether showed that the rate increased in the order, exo-cis > trans > endo-cis. And electron withdrawing substituents increased the rates. The field effect was suggested to explain these results.

Journal

  • NIPPON KAGAKU KAISHI

    NIPPON KAGAKU KAISHI 1975 (4), 652-656, 1975-04-10

    The Chemical Society of Japan

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