Kinetics and Mechanisms of the Acid-Catalyzed Hydrolyses of N-(4-Substitued-arylsulf inyl)phthalimides

Abstract

The acid-catalyzed hydrolyses of N-(4-substituted-arylsulfinyl)phthalimides were studied in aqueous solutions of perchloric and sulfuric acids at 50.0 ± 0.1 and of hydrochloric acid at 40.0 ± 0.1°C. Analysis of the data by the Cox-Yates excess acidity method and substituent, temperature and solvent isotope effects indicate hydrolysis by an A2 mechanism at low acidity. At higher acidities a changeover to an A1 mechanism is observed. Copyright © 2001 John Wiley & Sons, Ltd.