Intramolecular participation by the thiol group in amide hydrolysis: the general acid-catalyzed pathway

…, P Patterson, A Stevens-Whalley

Index: McDonald, Robert S.; Patterson, Patricia; Stevens-Whalley, Ann Canadian Journal of Chemistry, 1983 , vol. 61, p. 1846 - 1852

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Citation Number: 8

Abstract

ROBERT S. MCDONALD, PATRICIA PATTERSON, and ANN STEVENS-WHALLEY. Can. J. Chem. 61, 1846 (1983) Thc hydrolysis of Nn-propyl-2-mercaptomcthylbenzan~ ide has bcen investigated in HCI and a series of buffers over the pH region 0-8.5 at 40.0 C. p.= IO Nucleophilic participation by thc thiol group during amide hydrolysis produces 2- thiophthalide as the stable product. The sceond-order ratc constant for thc acid-catalyzed ...