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Interconversion among Dibromocyclopentene Isomers
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- Tsujita Kenji
- Department of Applied Chemistry, Graduate School of Engineering, Kyushu University | Konishiroku Photo Ind. Company Limited
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- Tanaka Ryuichi
- Department of Materials Science and Technology, Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
Bibliographic Information
- Other Title
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- 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.
Journal
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- 九州大学大学院総合理工学報告
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九州大学大学院総合理工学報告 2 (2), 27-35, 1981-01-20
Interdisciplinary Graduate School of Engineering Sciences, Kyushu University
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Details 詳細情報について
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- CRID
- 1390290699814936960
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- NII Article ID
- 120005371736
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- NII Book ID
- AN00055101
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- DOI
- 10.15017/17513
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- HANDLE
- 2324/17513
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- Text Lang
- ja
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- Article Type
- departmental bulletin paper
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- Data Source
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- JaLC
- IRDB
- CiNii Articles
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- Abstract License Flag
- Allowed