Dergiler / Turkish Journal of Chemistry / 2003 / Cilt: 27 - Sayı: 2
Studies on the Mechanism of Base-Catalyzed Decomposition of Bicyclic Endoperoxides
- Sayfa
- 145–154
- DOI
- —
Özet
Kinetic studies were performed to clarify the Kornblum-Delamare reaction mechanism of bicyclic endoperoxides. Ascaridol and 1,4-diphenyl-2,3-dioxa-bicyclo[2.2.2]oct-5-ene, not having a -protons, did not provide any reaction with bases. Reaction with different bases has revealed that reaction rates for the base-catalyzed decomposition of 2,3-dioxa-bicyclo[2.2.2]oct-5-ene depend strongly on the base strength. The stronger the base used, the faster the conversion rate. Reaction rate values k of endoperoxides with different skeletons were also studied with NEt3. It has been noted that the strength of the base plays the dominant role in determining the rate of the reactions.
Abstract
Kinetic studies were performed to clarify the Kornblum-Delamare reaction mechanism of bicyclic endoperoxides. Ascaridol and 1,4-diphenyl-2,3-dioxa-bicyclo[2.2.2]oct-5-ene, not having a -protons, did not provide any reaction with bases. Reaction with different bases has revealed that reaction rates for the base-catalyzed decomposition of 2,3-dioxa-bicyclo[2.2.2]oct-5-ene depend strongly on the base strength. The stronger the base used, the faster the conversion rate. Reaction rate values k of endoperoxides with different skeletons were also studied with NEt3. It has been noted that the strength of the base plays the dominant role in determining the rate of the reactions.