Kinetics and mechanisms of the acid-catalyzed hydrolyses of N-(4-Substitued-arylsulfinyl)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 degreesC. 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 Al mechanism is observed. Copyright (C) 2001 John Wiley & Sons, Ltd.