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Paper | Regular issue | Vol 53, No. 1, 2000, pp.55-68
Published online, 1st January, 1970
DOI: 10.3987/COM-99-8715
Photochemical Dimerization of Styrylnaphthofurans-II

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

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

Abstract

Irradiation of styrylnaphthofurans (3a, 3b) [10-1 M] (benzene) under anaerobic conditions gives mainly dimeric products (65-70%): [2+2] ethene-ethene cycloaddition products (9a, 9b, 10a, 10b and 11a, 11b) (40-44%) and [2+2] ethene-furan cycloaddition products (12a, 12b) (20-22%). Minor quantities of electrocyclization products (7a, 7b) (3.5-4.5%) and dihydrocyclization products (8a, 8b) (3-4.5%) are also isolated. The structures of the products are based on 1H and 13C NMR spectra, applying COSY, LR COSY, APT, HETCOR and NOESY techniques.