Aryl- and hetaryl-containing amide anions in reactions of aromatic nucleophilic substitution |
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| Authors: | V. M. Vlasov I. A. Os'Kina D. Landini A. Maia |
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| Affiliation: | (1) Novosibirsk Institute of Organic Chemistry, Siberian Branch of the Russian Academy of Sciences, 9 prosp. Akad. Lavrent'eva, 630090 Novosibirsk, Russian Federation;(2) Department of Organic and Industrial Chemistry, University of Milan, via Golgi 19, 20133 Milan, Italy |
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| Abstract: | The results of kinetic studies of SNAr reactions ofp-nitrohalobenzenes, hexafluorobenzene, and pentafluoropyridine with aryl-, diaryl-, and hetarylamide anions under homogeneous conditions (in dimethyl sulfoxide) and under conditions of phase transfer catalysis (in toluene) are analyzed. The increase in the Brönsted coefficient  Nu in reactions of amide anions in DMSO as the electrophilicity of the substrate increases and steric hindrance in nucleophiles decreases may result from a higher degree of charge transfer from a nucleophile to a substrate in the transition state. The possibility of replacement of the SNAr by the SET mechanism in these reaction is discussed.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2315–2319, December, 1995. |
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| Keywords: | aryl-containing amide anions aryl halides SNAr reactions phase transfer catalysis Brö nsted coefficient |
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