engleski

Photochemistry of Styryl-substituted Furo-benzobicyclo[3.2.1]octadiene Derivatives

The photochemistry of styryl substituted monofuran derivatives has been thoroughly investigated [1] in order to prepare furan polycyclic structures, potentially biologically active compounds. The irradiation of the unsubstituted furan derivative 1 resulted in intramolecular cycloaddition and efficient formation of the bicyclo[3.2.1]octadiene structure 2 via 1, 6-ring closure. No intramolecular cycloaddition product was found upon irradiation of o-vinylstyryl derivatives of naphtho[2, 1-b]furan 3 in which the furan ring is a part of the condensed systems [2]. Thus, it was of considerable interest from mechanistic and synthetic points of view, to try the photoreaction of styryl derivative of furo-benzobicyclo[3.2.1]octadiene 4 in order to prepare the naphthofuran derivative of benzobicyclo[3.2.1]octadiene 5. It is also expected that by ring closing of bicyclic styryl derivatives 4 (R = vinyl) a double bicyclic structure 6 with interesting stereochemistry could be obtained. [1] M. Šindler-Kulyk ; L. Špoljarić ; Ž. Marinić, Heterocycles 1989, 27, 679-682. [2] I. Škorić ; Ž. Marinić ; M. Šindler-Kulyk Heterocycles 2000, 53, 55-68.

photochemistry; bicyclo-octadiene; furan derivative; cycloaddition

nije evidentirano