Photooxygenation of 5- and 6-chloro-1,3-cycloheptadienes and reactions of their endoperoxides with base: effects of the chloro substituent on the reactions

Menzek A., SENGUL M., Cetinkaya Y., CEYLAN S.

JOURNAL OF CHEMICAL RESEARCH-S, sa.4, ss.209-214, 2005 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2005
  • Dergi Adı: JOURNAL OF CHEMICAL RESEARCH-S
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.209-214
  • Atatürk Üniversitesi Adresli: Evet

Özet

Photooxygenation reactions of 5- and 6-chlorocycloheptadienes 6 and 7 gave bicyclic endoperoxides 10-13. The endoperoxides 10 and 13 are major products due to the steric effects of the chloro substituent. The reactions of endoperoxide 10 with NEt3 under different conditions gave 1,4-epoxide 14, hydroxyenone 15, diketone 16, acetates 17-19 and diacetate 20. The reaction of endoperoxide 10 with pyridine and Ac2O gave diacetate 20 and dienone 21. The reaction of endoperoxide 13 with NEt3 gave tropone. The effects of the chloro substituent are discussed.