SCHEDULED MAINTENANCE
Penicilloic acid derivatives undergo two types of reversible thiazolidine ring opening reactions; in aqueous alkaline solution methyl benzylpenicilloate ring opens to give an enamine intermediate by a base-catalysed elimination process involving C-6-H whereas benzylpenicilloic acid epimerises at C-5 by unimolecular ring opening to form an intermediate iminium ion.
A. M. Davis and M. I. Page, J. Chem. Soc., Chem. Commun., 1985, 1702 DOI: 10.1039/C39850001702
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