Kinetics and mechanism of hydrolysis of N-acyloxymethyl derivatives of azetidin-2-one

E Valente, JRB Gomes, R Moreira…

Index: Valente, Emilia; Gomes, Jose R. B.; Moreira, Rui; Iley, Jim Journal of Organic Chemistry, 2004 , vol. 69, # 10 p. 3359 - 3367

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Citation Number: 9

Abstract

The pH-independent, acid-catalyzed and base-catalyzed hydrolyses of N- acyloxymethylazetidin-2-ones all occur at the ester function. The pH-independent hydrolysis involves rate-limiting alkyl CO fission and formation of an exocyclic β-lactam iminum ion. This iminium ion is then trapped by water at the exocyclic iminium carbon atom, rather than at the β-lactam carbonyl carbon atom, to form the corresponding N-hydroxymethylazetidin- ...