# Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers

## TL;DR

This study investigates the selective chemical breakdown of a specific compound and confirms the process using computational methods.

## Contribution

The paper presents new insights into the regioselective methanolysis of azido-4-nitrobenzoate epoxycyclooctane isomers using experimental and computational methods.

## Key findings

- Two chloro-acetate isomers were formed through methanolysis and acetylation.
- Crystallographic and NMR analyses confirmed the structures of the isomers.
- DFT computations validated the regioselectivity and efficiency of the methanolysis process.

## Abstract

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.