Effects of electron acceptors and radical scavengers on nonchain radical nucleophilic substitution reactions
- Lanzhou Univ. (China)
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.
- OSTI ID:
- 6131400
- Journal Information:
- Journal of Organic Chemistry; (United States), Journal Name: Journal of Organic Chemistry; (United States) Vol. 58:1; ISSN 0022-3263; ISSN JOCEAH
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ANIONS
AROMATICS
CARBANIONS
CHARGED PARTICLES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
DMSO
ELECTRON TRANSFER
ESTERS
HALOGENATED AROMATIC HYDROCARBONS
IONS
ORGANIC COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC SULFUR COMPOUNDS
RADICALS
SULFOXIDES
YIELDS