The complete conversion of the highly hindered ester, 2-carbamoylphenyl mesitoate, into the highly hindered amide, mesitamide, via base-catalysed intramolecular nucleophilic amide-group participation

Abstract

The intramolecular nucleophilic participation of a suitably located amide group is shown to promote the cleavage of a sterically hindered ester linkage with extreme readiness compared with cleavage induced by intermolecular attack by hydroxide ion. Steric shielding effects are utilised to suppress the incursion of competitive side-reactions and to show that under alkaline conditions nucleophilic attack by the amide group occurs entirely through nitrogen.