The hydrolytic reactivity of β-sultams

Abstract

N-Methyl β-sultam undergoes acid- and base-catalysed hydrolysis in water at 30 °C and I= 1.0 mol dm–3 with kH+= 2.79 dm3 mol–1s–1 and kOH= 1.38 × 10–2 dm3mol–1 s–1. These second-order rate constants are approximately 109 and 107, respectively, greater than those for a similar acyclic sulfonamide. The entropy of activation for the acid-catalysed hydrolysis of the β-sultam is –80 J K–1 mol–1 which may be indicative of unimolecular ring opening, whereas that for the base-catalysed reaction, –184 J K–1 mol–1, is consistent with a bimolecular process.