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■ Observation of the Primary Intermediates in the Photochemistry of o-Vinylstyrylfurans

Irena Skoric, Nikola Basaric, Zeljko Marinic, and Marija Sindler-Kulyk*

*Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulicev trg 20, P.O Box 177, HR-10000 Zagreb, Croatia

Abstract

The intermediates, 3a,9-dihydro-4,9-methano-4H-benzo[4,5]cyclohepta[1,2-b]furan (3a) and 5b,11-dihydro-6,11-methano-6H-benzo[4,5]cyclohepta[1,2-b]benzo[d]furan (3b), formed upon irradiation of 2-[2-(2-vinylphenyl)ethenyl]furan (1a) and 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (1b), respectively, are determined and spectroscopycally characterized. Whereas only the intermediate (3b) reacts photochemically with methanol to give the regioselective adduct (6b), both intermediates are trapped by molecular oxygen giving hydroproxides (7a,b), hydroxy- (8a,b) and keto derivatives (9a, b).