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Paper | Regular issue | Vol 51, No. 6, 1999, pp.1355-1369
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8502
Synthesis and Photochemistry of Styryl Substituted Annelated Furan Derivatives

Marija Sindler-Kulyk,* Irena Skoric, Slavica Tomsic, Zeljko Marinic, and Draginja Mrvos-Sermek

*Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulicev trg 19, P.O Box 177, HR-10000 Zagreb, Croatia

Abstract

New β-substituted benzo- and naphthofuryl derivatives (5, 6 and 7) of o-divinylbenzene, were synthesized and irradiated in order to form annelated bi-cyclo[3.2.1]octadienes. While 2-[2-(2-vinylphenyl)ethenyl]benzo[b]furan (5) upon irradiation gives the bicyclo[3.2.1]octadiene derivative (12) in 65% yield, 2-[2-(2-vinylphenyl)ethenyl]naphtho[2,1-b]furan (6) and 2-[2-(2-vinylphenyl)ethenyl]na-phtho[1,2-b]furan (7), undergo cis-trans-isomerization but not form intramole-cular photocycloaddition products. The mechanism of the intramolecular [2+2] photocycloaddition is explained via intermediate (17) which was proved by the formation of products (18) and (19), by irradiation in methanol and deuteromethanol.