Reactions of nitronates derived from simple nitro alkanes with some thio-stabilized cationic intermediates |
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Authors: | I. M. Lyapkalo M. I. Lazareva A. D. Dil'man S. L. Ioffe W. A. Smit |
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Affiliation: | (1) N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913 Moscow, Russian Federation;(2) Higher Chemical College, Russian Academy of Sciences, 9 Miusskaya pl., 125820 Moscow, Russian Federation |
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Abstract: | Trimethylsilyl and DBU nitronates derived from nitromethane and nitropropanes do not undergoC-alkylation by episulfonium (ESI) or thiophanium (TPI) cationic intermediates. The above-mentioned derivatives of 1-nitropropane react with ESI and TPI to give the corresponding products ofO-alkylation of 1-chloro-1-oxyiminopropane. The reactions of DBU nitronates derived from nitromethane and 2-nitropropane with ESI or TPI proceed asO-alkylation followed by standard fragmentation of the initially formed nitronate intermediates to give methyl (4-tolylthio)acetate or methyl 2,2-dimethyl-3-methyloxy-(4-tolylthio)butanoate respectively. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 492–498, March, 1999. |
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Keywords: | episulfonium ions thiophanium ions silyl nitronates aliphatic nitro compounds Lewis acids alkylation |
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