Mechanisms of hydrolysis of phenyl-and benzyl 4-nitrophenyl-sulfamate esters

WJ Spillane, S Thea, G Cevasco, MJ Hynes…

Index: Spillane, William J.; Thea, Sergio; Cevasco, Giorgio; Hynes, Michael J.; McCaw, Cheryl J. A.; Maguire, Neil P. Organic and Biomolecular Chemistry, 2011 , vol. 9, # 2 p. 523 - 530

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Citation Number: 8

Abstract

The kinetics of hydrolysis at medium acid strength (pH interval 2–5) of a series of phenylsulfamate esters 1 have been studied and they have been found to react by an associative SN2 (S) mechanism with water acting as a nucleophile attacking at sulfur, cleaving the S–O bond with simultaneous formation of a new S–O bond to the oxygen of a water molecule leading to sulfamic acid and phenol as products. In neutral to moderate ...