Reactivity and the mechanisms of reactions of β-sultams with nucleophiles

JM Wood, PS Hinchliffe, AP Laws…

Index: Wood, J. Matthew; Hinchliffe, Paul S.; Laws, Andrew P.; Page, Michael I. Journal of the Chemical Society. Perkin Transactions 2, 2002 , # 5 p. 938 - 946

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Citation Number: 25

Abstract

Ethane-1, 2-sultam has a pKa of 12.12±0.06 at 30° C and its rate of alkaline hydrolysis shows a pH-dependence reflecting this so that the observed pseudo first-order rate constant at pHs above the pKa are pH independent. There is no evidence of neighbouring group participation in the hydrolysis of either N-α-carboxybenzylethane-1, 2-sultam or N-( hydroxyaminocarbonylmethyl)-2-benzylethane-1, 2-sultam. Oxyanions, but not amines or ...