title: Synthesis and photochemistry of beta,beta'-di(2-furyl)-substituted o-divinylbenzenes: intra- and/or intermolecular cycloaddition as an effect of annelation.
abstract: New heteroaryl-substituted o-divinylbenzenes, 2,2'-(1,2-phenylenedivinylene)difuran (9), 2,2'-(1,2-phenylenedivinylene)bisbenzo[b]furan (10), and 2,2'-(1,2-phenylenedivinylene)bisnaphtho[2,1-b]furan (11), were prepared and irradiated at various concentrations; intramolecular photocycloaddition and intermolecular [2+2] twofold photoaddition reactions took place to give bicyclo[3.2.1]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-bicyclo[3.2.1]octadiene derivative 14 at low concentrations, and only the cyclophane derivative 17 at high concentrations.
authors.affiliation: Department of Organic Chemistry, Faculty of Chemical Engineering and Technology, University of Zagreb, Marulićev trg 19, 10000 Zagreb, Croatia.
authors.forename: Irena
authors.initials: I
authors.lastname: Skorić
authors.forename: Nikola
authors.initials: N
authors.lastname: Basarić
authors.forename: Zeljko
authors.initials: Z
authors.lastname: Marinić
authors.forename: Aleksandar
authors.initials: A
authors.lastname: Visnjevac
authors.forename: Biserka
authors.initials: B
authors.lastname: Kojić-Prodić
authors.forename: Marija
authors.initials: M
authors.lastname: Sindler-Kulyk