Mesoionic compounds. Part 6. Acid-catalysed hydrolysis of alkyloxatriazoles

Abstract

The acid-catalysed hydrolyses of isopropyl- and methyloxatriazole have been studied in aqueous solutions of mineral acids at 120°C. Analyses of the data by Bunnett–Olsen criteria, solvent deuterium isotope effects and entropies of activation are consistent with an A-1 mechanism for the hydrolysis of isopropyloxatriazole. On the other hand the hydrolysis of methyloxatriazole involves a rate-determining proton-transfer mechanism.