G. Olah, K. Y. Koltunov, G. Prakash
2004
Citations
0
Influential Citations
24
Citations
Journal
Heterocycles
Abstract
Isomeric 2-, 3- and 4-quinolinols (11-13) underwent selective ionic hydrogenation with cyclohexane in CF 3 SO 3 H-SbF 5 system to give 5,6,7,8-tetrahydro-2( 1 H)-quinolinone, 5,6,7,8-tetrahydro-3-quinolinol and 5,6,7,8-tetrahydro-4(1H)-quinolinone (28-30), respectively. When reaction was carried out in the presence of excess of aluminum chloride, 11 gave 3,4-dihydro-2(1H)-quinolinone (31), whereas 13 gave the product (30). Compounds (11) and (13) condense with benzene in the presence of aluminum halides producing phenyl substituted derivatives of 28, 31 and 30 (products 32-34), respectively. The mechanism of these and related reactions involving superelectrophilic dicationic intermediates is discussed.