Thermal Rearrangement of N-Alkyl-, and N-Aryl-(2,2-dihalo-1-phenylcyclopropyl)methyleneamines to 1-Alkyl-,and 1-Aryl-2 (or 3)-halo-4-phenylpyrroles

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著者

    • KAGABU Shinzo
    • Department of CHemistry, Faculty of Education, Gifu University
    • TSUJI Hideaki
    • Department of CHemistry, Faculty of Education, Gifu University
    • KAWAI Itsumi
    • Department of CHemistry, Faculty of Education, Gifu University
    • OZEKI Hitomi
    • Department of CHemistry, Faculty of Education, Gifu University

抄録

The thermolysis of <i>N</i>-<i>t</i>-alkyl-, and <i>N</i>-aryl-(2,2-dichlorocyclopropyl)methyleneamines yielded directly 1-<i>t</i>-alkyl, and 1-aryl-3-chloropyrroles as the major products along with a slight amount of the 2-chloro isomers. The transformation to the 3-chloropyrroles was enhanced in polar solvents. But basic additives directed the thermal rearrangement into the 1,2-bond cleavage of the cyclopropane ring, leading to the 2-chloropyrroles. On the other hand, (difluorocyclopropyl)methyleneamines were pyrolyzed exclusively to 3-fluoropyrroles under 1,3-bond cleavage. The ionic mechanism involving a heterolytic dissociation of chlorine atom under 1,3-bond scission of the cyclopropane ring is proposed for the rearrangement to 3-chloropyrroles, while a homolytic cleavage pathway is proposed for 3-fluoropyrroles. The present thermolysis supplies a unique preparative tool for 2-, and 3-halo-4-phenylpyrrole derivatives.

収録刊行物

  • Bulletin of the Chemical Society of Japan

    Bulletin of the Chemical Society of Japan 68(1), 341-349, 1995-01-15

    公益社団法人 日本化学会

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各種コード

  • NII論文ID(NAID)
    10008885297
  • NII書誌ID(NCID)
    AA00580132
  • 本文言語コード
    ENG
  • 資料種別
    ART
  • ISSN
    00092673
  • データ提供元
    CJP書誌  J-STAGE 
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