A general acid-catalyzed anion breakdown associated with an E1cB reaction in the hydrolysis of aryl N-(substituted phenylsulfonyl) carbamates

…, M Bergon, C Bergonzi, P Tisnes

Index: Vigroux, Alain; Bergon, Michel; Bergonzi, Catherine; Tisnes, Pierre Journal of the American Chemical Society, 1994 , vol. 116, # 26 p. 11787 - 11796

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Citation Number: 22

Abstract

Abstract: The hydrolysis of aryl N-(substituted phenylsulfony1) carbamates at 50" C in the pH range 0-13.5 leading to substituted benzenesulfonamides and phenols involves acyl group transfer. Reaction rates were measured spectrophotometrically and are independent of the concentration of the catalyst for buffers of PKBH> 8. With more acidic buffers, a general acid catalysis is observed for the hydrolysis of phenyl N-(phenylsulfony1) carbamate la (pKa= ...