Mesoionic compounds. Part 7. Acid catalysed hydrolysis of ethyloxatriazole
Abstract
The acid catalysed hydrolysis of ethyloxatriazole has been studied in aqueous solutions of mineral acids at 120 °C. Analyses of the data by Bunnett and Bunnett–Olsen criteria and entropies of activation are consistent with a gradual change-over from an A-2 mechanism at low acid concentration to a predominantly A-1 mechanism at high acidities. Values of the kinetic solvent isotope effect indicate the involvement of a modified A-2 mechanism in which a proton transfer is partially rate determining.