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.
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 492–498, March, 1999.
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Lyapkalo, I.M., Lazareva, M.I., Dil'man, A.D. et al. Reactions of nitronates derived from simple nitro alkanes with some thio-stabilized cationic intermediates. Russ Chem Bull 48, 488–494 (1999). https://doi.org/10.1007/BF02496167
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DOI: https://doi.org/10.1007/BF02496167