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Nucleophilic Substitution Reaction of p ‐Dinitrobenzene by a Carbanion: Evidence for Electron Transfer Mechanism
Author(s) -
Liu YouCheng,
Zhang KaiDong,
Liu JianMing,
Wu LongMin,
Liu ZhongLi
Publication year - 2002
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.20020201151
Subject(s) - chemistry , carbanion , dinitrobenzene , nucleophilic substitution , medicinal chemistry , photochemistry , nucleophilic aromatic substitution , substitution reaction , dimethyl sulfoxide , salt (chemistry) , sn2 reaction , electron transfer , reaction mechanism , organic chemistry , catalysis
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.