engleski

Synthesis and Photochemical Reactions of 2, 3-distyrylfurans

The photochemistry of styryl substituted monofuran derivatives has been thoroughly investigated (1). The irradiation of disubstituted o-divinylbenzenes, compounds 1a-c, resulted in the formation of bicyclo[3.2.1]octadiene structures 2, cyclophanes 3 and cyclobutanes 4 (2). With a view to study the hexatriene system in which the central double bond is a part of a furan ring various 2, 3-distyrylfurans 5 are prepared. The multistep synthesis of 5a-d was performed by the Wittig reactions of properly 3-substituted-2-furancarboxaldehydes and corresponding phosphonium salts. The irradiation of 2, 3-distyrylfurans 5 gave stilbenyl-like and phototransposition products. No intramolecular cycloadditions and formation of the bicyclic structures have been observed. The structure determination as well as the reaction mechanism will be discussed.

furans; photoreactions; polycyclic structures; photocycloaddition; o-divinylbenzenes; bicyclic structures; cyclophanes; phototransposition products

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