| Nucleophilic Substitution Reaction of p-Dinitrobenzene by a Carbanion: Evidence for Electron Transfer Mechanism |
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| 引用本文： | 刘有成,张凯东,吕建明,吴隆民,刘中立. Nucleophilic Substitution Reaction of p-Dinitrobenzene by a Carbanion: Evidence for Electron Transfer Mechanism[J]. 中国化学, 2002, 20(11): 1453-1456. DOI: 10.1002/cjoc.20020201151 |
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| 作者姓名： | 刘有成 张凯东 吕建明 吴隆民 刘中立 |
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| 作者单位： | LIU，You-Cheng，a，b ZHANG，Kai-Dong a L，Jian-Ming a WU，Long-Min a LIU，Zhong-Li a a National Laboratory of Applied Organic Chemistry，Lanzhou University，Lanzhou，Gansu 730000，China b Department of Chemistry，University of Sci |
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| 基金项目： | theNationalNaturalScienceFoundationofChina (Nos.2 9832 0 40and 2 0 0 72 0 36 )andtheSpecialFundforDoc toralProgramfromtheMinistryofEducationofChina |
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| 摘 要： | ＩｎｔｒｏｄｕｃｔｉｏｎＳｉｎｇｌｅｅｌｅｃｔｒｏｎｔｒａｎｓｆｅｒｉｎａｒｏｍａｔｉｃｎｕｃｌｅｏｐｈｉｌｉｃｓｕｂ ｓｔｉｔｕｔｉｏｎｈａｓａｔｔｒａｃｔｅｄｍｕｃｈａｔｔｅｎｔｉｏｎｉｎｒｅｃｅｎｔｙｅａｒｓ .Ｉｎａｄｄｉｔｉｏｎｔｏｔｈｅｗｅｌｌ ｋｎｏｗｎＳＲＮ1ｍｅｃｈａｎｉｓｍｒｅｐｏｒｔｅｄｂｙＢｕｎｎｅｔｔ,1ｍａｎｙｏｔｈｅｒａｃｔｉｖａｔｅｄａｒｏｍａｔｉｃｓｙｓｔｅｍｓ ,ｉ .ｅ .,ｎｉｔｒｏａｒｙｌｈａｌｉｄｅｓ ,ｄｉｎｉｔｒｏｂｅｎｚｅｎｅｓ ,ｅｔｃ .,ｈａｖｅｂｅｅｎｒｅ ｐ…
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| 关 键 词： | single electron transfer p-dinitrobenzene radical anion α-cyanoacetate carbanion retarding effect |
Nucleophilic Substitution Reaction of p-Dinitrobenzene by a Carbanion: Evidence for Electron Transfer Mechanism |
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| You‐Cheng Liu,Kai‐Dong Zhang,Jian‐Ming Liu,Long‐Min Wu,Zhong‐Li Liu. Nucleophilic Substitution Reaction of p-Dinitrobenzene by a Carbanion: Evidence for Electron Transfer Mechanism[J]. Chinese Journal of Chemistry, 2002, 20(11): 1453-1456. DOI: 10.1002/cjoc.20020201151 |
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| Authors: | You‐Cheng Liu Kai‐Dong Zhang Jian‐Ming Liu Long‐Min Wu Zhong‐Li Liu |
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| Abstract: | On the basis of investigation of cyclic voltammetry, EPR spectroscopy and competition experiments, the nucleophilic substitution reaction of p‐ dinitrobenzene with the sodium salt of ethyl α‐cyanoacetate carbanion in dimethyl sulfoxide giving ethyl α‐cyano‐α‐ (p‐nitrophenyl) acetate is shown to take place via the intermediacy of p‐dinitrobenzene radical anion. The reaction rate goes faster than that between p‐nitrohalobenzenes and the same sodium salt of ethyl α‐cyanoacetate carbanion. There is an evidence for a single electron transfer mechanism. |
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| Keywords: | single electron transfer p‐dinitrobenzene radical anion α‐cyanoacetate carbanion retarding effect |
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