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, cilt.83, sa.3, ss.227-235, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 83 Sayı: 3
  • Basım Tarihi: 2005
  • Doi Numarası: 10.1139/v05-046
  • Dergi Adı: CANADIAN JOURNAL OF CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.227-235
  • Atatürk Üniversitesi Adresli: Evet

Özet

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.