An unprecedented Co-II-tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides: A new approach to substituted furofuran systems

Sengul M., Simsek N., Balci M.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, sa.7, ss.1359-1363, 2000 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2000
  • Dergi Adı: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1359-1363
  • Anahtar Kelimeler: endoperoxides, cycloheptatriene, dichloroketene, singlet oxygen, cobalt, porphyrins, furofurans, BAEYER-VILLIGER OXIDATION, MICROBIOLOGICAL TRANSFORMATIONS, STEREOSELECTIVE SYNTHESES, CYCLO-ADDITIONS, CYCLOADDITIONS, DICHLOROKETENE, REARRANGEMENT, ROUTE, SALTS
  • Orta Doğu Teknik Üniversitesi Adresli: Hayır

Özet

Co-II-tetraphenylporphyrin-catalyzed decomposition of bicyclic endoperoxides 4 and 5 with a strained double bond moiety has been studied. Compounds 4 and 5 have been synthesized by photooxygenation of 3 which itself was obtained by dichloroketene addition to cycloheptatriene, followed by removal of the chlorine atoms. An unusual decomposition mode of 4 promoted by Co-II-TPP resulted in the formation of 8 and 9 which are important building blocks in furofuran systems.