The acid catalysed hydrolysis of N-t-butylbenzaldoxime and 2-t-butyl-3-phenyloxaziridine

Abstract

The rates of hydrolysis of N-t-butylbenzaldoxime and 2-t-butyl-3-phenyloxaziridine have been measured over a wide range of acidities in HCl, H₂SO₄, and HClO₄. Interpretation of the rate data by use of the Bunnett criteria of mechanism, deuterium isotope effects, and Arrhenius parameters are consistent with a bimolecular specific acid catalysed mechanism for hydrolysis of both substrates reacting through the protonated nitrone as a common intermediate.