Synthesis and photochemistry of beta,beta'-di(2-furyl)-substituted o-divinylbenzenes: intra- and/or intermolecular cycloaddition as an effect of annelation |
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Authors: | Skori? Irena Basari? Nikola Marini? Zeljko Visnjevac Aleksandar Koji?-Prodi? Biserka Sindler-Kulyk Marija |
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Institution: | Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Maruli?ev trg 19, 10000 Zagreb, Croatia. |
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Abstract: | New heteroaryl-substituted o-divinylbenzenes, 2,2'-(1,2-phenylenedivinylene)difuran (9), 2,2'-(1,2-phenylenedivinylene)bisbenzob]furan (10), and 2,2'-(1,2-phenylenedivinylene)bisnaphtho2,1-b]furan (11), were prepared and irradiated at various concentrations; intramolecular photocycloaddition and intermolecular 2+2] twofold photoaddition reactions took place to give bicyclo3.2.1]octadiene derivatives 12-14 and cyclophane derivatives 15-17, respectively. Compound 11 was the most selective of these o-divinylbenzenes, which, owing to pi-pi intra- or intermolecular complexation, gave only the exo-bicyclo3.2.1]octadiene derivative 14 at low concentrations, and only the cyclophane derivative 17 at high concentrations. |
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Keywords: | cycloaddition cyclophanes dimerization heteroaromatics photochemistry |
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