The regioselective methanolysis of new azido-4-nitrobenzoate epoxycyclooctane isomers and the characterization of the resulting products are described herein. Firstly, treatment of key compound 8-azidocyclooct-4-en-1-ol with 4-nitrobenzoyl chloride followed by an epoxidation reaction and then methanolysis of the epoxide ring and acetylation resulted in the formation of two corresponding chloro-acetate isomers. The structure of one of the chloro-acetate isomers was determined via crystallographic analysis and the other by 1D and 2D NMR spectroscopy. DFT computations confirm the regioselectivity of the methanolysis process, highlighting its precision and efficiency.
Polat et al. (Thu,) studied this question.