Acid-and base-dependent hydrolysis of N-(sulfonatooxy)-3-bromoacetanilide: involvement of N-(3-bromophenyl) hydroxylamine O-sulfonate

…, M Pelecanou, JJ Mulero, RK Lagerman

Index: Novak, Michael; Rovin, Lise H.; Pelecanou, Maria; Mulero, Julio J.; Lagerman, Robert K. Journal of Organic Chemistry, 1987 , vol. 52, # 10 p. 2002 - 2010

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Citation Number: 10

Abstract

N-(Sulfonatooxy)-3-bromoacetanilide (le) undergoes hydrolysis at 80" C in the range pH 1.0- 8.0 by acid-and base-dependent processes and by an uncatalyzed path. The uncatalyzed reaction exhibits the same characteristics as the uncatalyzed NO bond-cleavage reactions of the more reactive N-(su1fonatooxy) acetanilides. The pH-dependent pathways involve the hydrolysis of le to form N-(3-bromophenyl) hydroxylamine-O-sulfonate (2). This material ...