Superacid catalyzed reactions of 5-amino-1-naphthol with benzene and cyclohexane

5-Amino-1-naphthol undergoes ionic hydrogenation with cyclohexane and condenses with benzene when reacted in the presence of excess of aluminum halides to give 5-amino-1-tetralone (10) and 5-amino-3-phenyl-1-tetralone, respectively. In CF3SO3H as well as CF3SO3H-SbF5 superacidic media 5-amino-1-naphthol gave N,C-diprotonated dication that can be considered as the superelectrophilic intermediate in the reactions with cyclohexane and benzene. The mechanism of these reactions is discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.