The methyl (la) and the phenyl (2) derivatives of (Z)-4-benzylideneoxazolin-5-one were hydrolyzed at comparable rates under alkaline conditions. In contrast, the acidic hydrolysis of 2 was at least 105 times slower than that of la. The Hammett p value obtained from the acidic hydrolysis of the phenyl substituted derivatives of la was 0.20 ± 0.09 while that from the corresponding basic hydrolysis was 1.50 ± 0.11. Methanolysis of la under basic conditions produced the methyl ester of (Z)-a-(acetylamino)cinnamic acid, and that under acidic conditions led to products consistent with the attack of methanol at the imine carbon. These results indicate that the alkaline hydrolysis of the oxazolin-5-one derivatives occurs through nucleophilic attack at the carbonyl carbon of the substrate and the acidic hydrolysis through that at the imine carbon.
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