Reactions of nitronates derived from simple nitro alkanes with some thio-stabilized cationic intermediates

Article abstract of DOI:10.1007/BF02496167

Trimethylsilyl and DBU nitronates derived from nitromethane and nitropropanes do not undergo C-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 of O-alkylation of 1-chloro-1-oxyiminopropane. The reactions of DBU nitronates derived from nitromethane and 2-nitropropane with ESI or TPI proceed as O-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.