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, no.7, pp.1359-1363, 2000 (Peer-Reviewed Journal) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2000
  • Journal Name: EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
  • Journal Indexes: Science Citation Index Expanded, Scopus
  • Page Numbers: pp.1359-1363
  • Keywords: endoperoxides, cycloheptatriene, dichloroketene, singlet oxygen, cobalt, porphyrins, furofurans, BAEYER-VILLIGER OXIDATION, MICROBIOLOGICAL TRANSFORMATIONS, STEREOSELECTIVE SYNTHESES, CYCLO-ADDITIONS, CYCLOADDITIONS, DICHLOROKETENE, REARRANGEMENT, ROUTE, SALTS

Abstract

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.