Effects of Electron Acceptors and Radical Scavengers on Nonchain Radical Nucleophilic Substitution Reactions

Article abstract of DOI:10.1021/jo00053a040

The yields of reaction products from thermal nucleophilic substitution reactions in dimethyl sulfoxide (DMSO) of six o- and p-nitrohalobenzenes (1) with sodium salt of ethyl α-cyanoacetate carbanion (2) were found to be markedly diminished by addition of small amounts of strong electron acceptors (p-dinitrobenzene, m-dinitrobenzene, and o-dinitrobenzene) (Table II), but little or no diminished effects on the yields of reaction products were observed by addition of radical scavengers ( such as galvinoxyl, nitroxyl, etc.) (Table III).The results are consistent with the conclusion that these reactions proceed via a nonchain radical nucleophilic substitution mechanism.