Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids

Konstantin Yu Koltunov; G K Surya Prakash; Golam Rasul; George A Olah

doi:10.1021/jo020099n

Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids

J Org Chem. 2002 Jun 14;67(12):4330-6. doi: 10.1021/jo020099n.

Authors

Konstantin Yu Koltunov¹, G K Surya Prakash, Golam Rasul, George A Olah

Affiliation

¹ Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles 90089-1661, USA.

PMID: 12054971
DOI: 10.1021/jo020099n

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.