Maeda, Hajime Matsuda, Shoji Mizuno, Kazuhiko Intramolecular Photocycloaddition Reactions of Arylcyclopropane Tethered 1‑Cyanonaphthalenes Intramolecular photocycloaddition reactions of 1-cyanonaphthalenes bearing an arylcyclopropane containing side chain were investigated. Photoreactions of members of this family in which the arylcyclopropane moiety is bonded at the 2-position of the 1-cyanonaphthalene ring produce head-to-head and head-to-tail 1,2-[3+2] photocycloadducts. On the other hand, substances in this family containing an arylcyclopropane side chain linked to the 4-position of the cyanoarene ring undergo photoreactions to form [4+3] photocycloadducts along with novel nine-membered ring products, which are produced by photochemically induced 10π conrotatory ring opening of the initially formed intramolecular [3+2] cycloadducts. The results of solvent effects and fluorescence investigations along with those focusing on corresponding intermolecular photoreactions demonstrate that the photocycloadducts are formed predominantly through an intramolecular exciplex mechanism and that a photoinduced intramolecular electron transfer pathway via zwitterionic biradicals might be partly responsible for the process when CH<sub>3</sub>CN is the solvent. zwitterionic biradicals;1- cyanonaphthalene ring;side chain;4- position;arylcyclopropane side chain;arylcyclopropane moiety;10π conrotatory ring opening;novel nine-membered ring products;Intramolecular Photocycloaddition Reactions;photocycloadduct;intramolecular exciplex mechanism;photoreaction;1- cyanonaphthalenes;CH 3 CN;cyanoarene ring;fluorescence investigations;2- position;photoinduced intramolecular electron transfer pathway 2016-08-22
    https://acs.figshare.com/articles/dataset/Intramolecular_Photocycloaddition_Reactions_of_Arylcyclopropane_Tethered_1_Cyanonaphthalenes/3793227
10.1021/acs.joc.6b01721.s001