Koltunov Konstantin Yu, Prakash G K Surya, Rasul Golam, Olah George A
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles 90089-1661, USA.
J Org Chem. 2002 Jun 14;67(12):4330-6. doi: 10.1021/jo020099n.
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.
异构的5-、6-、7-羟基喹啉（11 - 13）和5-羟基异喹啉（14）在CF(3)SO(3)H - SbF(5)超酸介质中生成N,C-双质子化双阳离子。化合物11、13、14和8-羟基喹啉（5）在氯化铝存在下与环己烷发生选择性离子氢化反应。化合物11和14在卤化铝存在下与苯缩合。讨论了涉及超亲电双阳离子中间体的详细反应机理。
