Experimental and DFT studies on the regioselective methanolysis of 5-azido-9-oxabicyclo[6.1.0]nonan-4-yl 4-nitrobenzoate isomers
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, cilt.22, sa.1, ss.547-556, 2026 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 22 Sayı: 1
- Basım Tarihi: 2026
- Doi Numarası: 10.3762/bjoc.22.40
- Dergi Adı: BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Directory of Open Access Journals, Natural Science Collection (ProQuest), Biological Science Database (ProQuest)
- Sayfa Sayıları: ss.547-556
- Anahtar Kelimeler: azides, 8-azidocyclooct-4-en-1-yl 4-nitrobenzoate, DFT, epoxycyclooctane azide, methanolysis
- Hakkari Üniversitesi Adresli: Evet
Özet
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.