Interconversion among Dibromocyclopentene Isomers

DOI IR (HANDLE) Open Access
  • Tsujita Kenji
    Department of Applied Chemistry, Graduate School of Engineering, Kyushu University | Konishiroku Photo Ind. Company Limited
  • Tanaka Ryuichi
    Department of Materials Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University

Bibliographic Information

Other Title
  • ジブロムシクロペンテンの異性体間相互変換反応

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Description

Trans-3,4, Trans-3,5-, and cis-3, 5-dibromocyclopentenes (1, 2, and 3) underwent facile interconversions in chloroform in the presence of a catalytic amount of tetraethylammonium bromide. The isomerizations involved the nucleophilic attacks by the added bromide ions to these allylic systems through both the S_N2 and S_N2' mechanisms. The S_N2' reactions were associated with syn stereospecificity, and proceeded at rates ca. 1/10 those of the S_N2 reactions. In the absence of added ammonium salt, isomers 1 and 2 isomerized into one another, but isomer 3 remained intact.

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Details 詳細情報について

  • CRID
    1390290699814936960
  • NII Article ID
    120005371736
  • NII Book ID
    AN00055101
  • DOI
    10.15017/17513
  • HANDLE
    2324/17513
  • Text Lang
    ja
  • Article Type
    departmental bulletin paper
  • Data Source
    • JaLC
    • IRDB
    • CiNii Articles
  • Abstract License Flag
    Allowed

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