Studies on the mechanism of base-catalyzed decomposition of bicyclic endoperoxides

Mete E., Altundas R., Secen H., Balci M.

TURKISH JOURNAL OF CHEMISTRY, vol.27, no.2, pp.145-153, 2003 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 27 Issue: 2
  • Publication Date: 2003
  • Journal Name: TURKISH JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus, TR DİZİN (ULAKBİM)
  • Page Numbers: pp.145-153
  • Middle East Technical University Affiliated: No

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 alpha-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.