Reaction of N-substituted Exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamides with Acetic Acid

Acylation of N-substituted exo-2-hydroxy-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamides on heating in boiling glacial acetic acid gave the corresponding trans-diacetoxy imides of the norbornane series. The effect of the reaction time on the product composition was studied in the reaction with exo-2-hydroxy-N-(4-methylphenyl)-5-oxo-4-oxatricyclo[4.2.1.03,7]nonane-endo-9-carboxamide. The structure of the resulting norbornane-2,3-dicarboximides was confirmed by IR, 1H NMR, and mass spectra, and the structure of N-(2,5-dimethylphenyl)-exo-2,endo-3-diacetoxybicyclo[2.2.1]heptan-endo-5,endo-6-dicarboximide was additionally proved by X-ray analysis.