Substituent effects of the cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the benzocycloheptene endoperoxides

Guney M., Ceylan Z., Dastan A., Balci M.

CANADIAN JOURNAL OF CHEMISTRY, vol.83, no.3, pp.227-235, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 83 Issue: 3
  • Publication Date: 2005
  • Doi Number: 10.1139/v05-046
  • Journal Name: CANADIAN JOURNAL OF CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.227-235
  • Middle East Technical University Affiliated: No

Abstract

The cycloaddition reaction of 7-substituted 5H-benzocycloheptenes with singlet oxygen and the chemistry of the obtained endoperoxides were investigated. Reaction of carboethoxy-substituted endoperoxide with NEt3 gave a mixture of products; hydroxyketone, diketone, and carboethoxy-substituted keto-enol tautomers, whereas the reaction of methyl-substituted endoperoxide only formed a diketone under the same reaction conditions. Thermolysis, thiourea, and CoTPP reactions of the endoperoxides were also studied. The reaction mechanism and electronic effect of substituents were discussed.