Acid-catalysed hydrolysis of some aromatic cyclic sulfamates

Abstract

The acid catalysed hydrolysis of some cyclic sulfamates, X-3-(p-tolylsulfonyl)-1,2,3-benzoxathiazole 2,2-dioxides (1a X=Me; 1b, X=H; 1c, X= Cl; 1d, X=NO2) have been studied in concentrated aqueous sulfuric and perchloric acid solutions. Analysis of the data by the Excess Acidity Method, activation parameters, substituent, solvent deuterium isotope effect and order of the catalytic effects of the acids are all in agreement with an A-1 mechanism in the studied range.