Introduction of Sulfur Atoms into Trifluoromethylated Alkenyl Sulfones and Chlorides Using a Reactive Sulfur-Graphite Electrode
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- KUNUGI Akira
- Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
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- JABBAR Md. Abdul
- Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
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- NAITOH Shuichi
- Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
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- YASUZAWA Mikito
- Department of Chemical Science and Technology, Faculty of Engineering, The University of Tokushima
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- UNO Hidemitsu
- Advanced Instrumentation Center for Chemical Analysis, Ehime University
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<p>The introduction of sulfur atoms into trifluoromethylated alkenyl sulfones and chlorides were studied using a reactive sulfur-graphite electrode in N,N-dimethylformamide. A substrate, 2-(4-biphenylyl)-4,4,4-trifluoro-3-phenylsulfonyl-2-butenenitrile (1a) afforded a coupling compound bridged with a nitrogen atom of isothiazole and 1,2-dithiolane skeleton (2). 1-(4-Biphenylyl)-3,3,3-trifluoro-2-phenylsulfonylpropene (1b) without a cyano group gave a complex oligomeric compound (3) without the elimination of the phenylsulfonyl group. 2-(4-Biphenylyl)-3-chloro-4,4,4-trifluoro-2-butenenitrile (1c) having a chloro group as a leaving group gave 2,4-di (4-biphenylyl)-2,4-dicyano-l ,5-bis(trifluoromethyl)-3, 6-dithiabicyclo [3.1.0] hexane (4) and 2-(4-biphenylyl)-4,4,4-trifluoro-2-butenenitrile (5). Methyl 2-(4-biphenylyl)-3-chloro-4,4,4-trifluoro-2-butenoate (1d) having an ester group in the place of a cyano group afforded di- [2-(4 biphenylyl)-2-methoxycarbonyl-1-trifluoromethylethyl] disulfide (6). The formation of such sulfur-containing organofluorine compounds except for the oligomeric compound 3 is characterized as the addition of polysulfide anion(s) produced by electroreduction of elemental sulfur, followed by the elimination of the phenylsulfonyl or the chloro group.</p>
収録刊行物
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- Electrochemistry
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Electrochemistry 68 (12), 955-962, 2000-12-05
公益社団法人 電気化学会
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詳細情報 詳細情報について
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- CRID
- 1390564227344490240
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- NII論文ID
- 10005749156
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- NII書誌ID
- AN00151637
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- ISSN
- 21862451
- 13443542
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- NDL書誌ID
- 5589154
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- 本文言語コード
- en
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- データソース種別
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- JaLC
- NDL
- Crossref
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- 抄録ライセンスフラグ
- 使用可