title: Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids.
abstract: Isomeric 5-, 6-, 7-hydroxyquinolines (11-13) and 5-hydroxyisoquinoline (14) gave N,C-diprotonated dications in CF(3)SO(3)H-SbF(5) superacid medium. Compounds 11, 13, 14, and 8-hydroxyquinoline (5) underwent selective ionic hydrogenation with cyclohexane in the presence of aluminum chloride. Compounds 11 and 14 condense with benzene in the presence of aluminum halides. The detailed mechanism of reactions, which involves superelectrophilic dicationic intermediates, is discussed.
authors.affiliation: Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles 90089-1661, USA.
authors.forename: Konstantin Yu
authors.initials: KY
authors.lastname: Koltunov
authors.forename: G K Surya
authors.initials: GK
authors.lastname: Prakash
authors.forename: Golam
authors.initials: G
authors.lastname: Rasul
authors.forename: George A
authors.initials: GA
authors.lastname: Olah