Aromatic Nucleophilic Substitution. 20. Kinetics of the Reaction of 2-(Acetylamino)ethyl 2,6-Dinitrophenyl Ether and N-Acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline with Potassium Methoxide in Me2SO-Methanol

Article abstract of DOI:10.1021/jo00187a015

The reactions of 2-(acetylamino)ethyl 2,6-dinitrophenyl ether (1e) and N-acetyl-N-(2-hydroxyethyl)-2,6-dinitroaniline (6e) with potassium methoxide were carried out in Me2SO-MeOH (60:40, v/v).In both reactions the same spiro anionic ? complex 3e was formed, although the two rates of formation of 3e were different.On the other hand, the rates of decomposition of 3e were the same in both reactions within experimental error, both indicating that considerable amounts of 1e and 6e are initially converted into 3e, which then undergoes unimolecular decomposition.