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

• İlknur Polat,
• Selçuk Eşsiz and
• Emine Salamci

Beilstein J. Org. Chem. 2026, 22, 547–556, doi:10.3762/bjoc.22.40

• process, highlighting its precision and efficiency. Keywords: azides; 8-azidocyclooct-4-en-1-yl 4-nitrobenzoate; DFT; epoxycyclooctane azide; methanolysis; Introduction Organic azides are very important precursors for the preparation and synthesis of various nitrogen-containing compounds, as well as

• -oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers starting from cis,cis-1,5-cyclooctadiene. Results and Discussion For the synthesis of the hitherto unknown key compound 8-azidocyclooct-4-en-1-yl 4-nitrobenzoate (8), we commenced by obtaining the known 5,6-epoxycyclooctene (6), which was prepared by

• NMR (100 MHz, CDCl3) δ 130.3, 127.5, 73.1, 66.8, 32.4, 29.7, 23.5, 23.1. (1S*,8S*,Z)-8-Azidocyclooct-4-en-1-yl 4-nitrobenzoate (8) The azidol 7 (0.50 g, 2.99 mmol) was dissolved in 9 mL of anhydrous pyridine and the solution was cooled to 0 °C. p-Nitrobenzoyl chloride (1.11 g, 5.98 mmol) and 4