Abstract
The yields of reaction products from thermal nucleophilic substitution reactions in dimethyl sulfoxide (DMSO) of six o- and p-nitrohalobenzenes with the sodium salt of ethyl [alpha]-cyanoacetate carbanion [Na[sup +][sup [minus]]CH(CN)CO[sub 2]Et] were found to be markedly diminished by addition of small amounts of strong electron acceptors (p-dinitrobenzene, m-dinitrobenzene, and o-dinitrobenzene), but little or no diminished effects on the yields of reaction products were observed by addition of radical scavengers (such as galvinoxyl, nitroxyl, etc.). The results are consistent with the conclusion that these reactions proceed via a nonchain radical nucleophilic substitution mechanism. 28 refs., 3 tabs.
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