A distorted amide (homobenzoquinuclidone, I) is shown to be remarkably susceptible toward attack by dicarboxylic acids capable of forming cyclic anhydrides. The hydrolytic process involves reversible nucleophilic attack to form a linear (open) anhydride. If no second carboxylate is present, or if the remote C02H unit is incapable of forming a stable cyclic anhydride, the open anhydride rapidly reverses to re-form I. In the presence of a second carboxylate that is in proximity to the open anhydride, nucleophilic attack occurs to give the amino acid of I and a cyclic anhydride of the diacid. The reaction pH vs log k2oM profiles for succinate, glutarate, and m-cyclopropane-1,2-dicarboxylic acid show three domains corresponding to attack of the monoanion of the diacid on I-H+, monoanion on I, and attack of the dianion on I. The relevance of these observations
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