engleski

Functionalization of the benzobicyclo[3.2.1]octadiene skeleton via photocatalytic and thermal oxygenation of a furan derivative

A simple and efficient protocol is utilized for the synthesis of novel functionalized benzobicyclo[3.2.1]octadiene derivatives by photocatalytic oxygenation of a furan derivative using an anionic free-base porphyrin as well as cationic and anionic manganese(III) porphyrins under different reaction conditions. The course and yields of these reactions were compared to those of the thermal reaction using m- chloroperbenzoic acid as oxidizing agent. The deviating reaction pathways with anionic and cationic metalloporphyrins may be attributed to simultaneous electronic and steric effects. Application of free-base and metalated water- soluble porphyrins for photocatalytic oxygenation of the furan ring fused to the rigid methano- bridged skeleton proved to be regioselective and flexible compared to the thermal reactions with mCPBA, giving at the same time novel potentially biologically active bicyclo[3.2.1]octenes with the basic skeleton of which is incorporated in many natural compounds.

benzobicyclo[3.2.1]octadienes ; furan derivative ; photocatalytic oxygenation ; porphyrins

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