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An Unprecedented Co II ‐Tetraphenylporphyrin‐Catalyzed Decomposition of Bicyclic Endoperoxides: A New Approach to Substituted Furofuran Systems
Author(s) -
Sengul Mehmet Emin,
Simsek Nermin,
Balci Metin
Publication year - 2000
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200004)2000:7<1359::aid-ejoc1359>3.0.co;2-b
Subject(s) - chemistry , bicyclic molecule , tetraphenylporphyrin , moiety , nitrene , cycloisomerization , decomposition , catalysis , photochemistry , medicinal chemistry , stereochemistry , organic chemistry , porphyrin
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.