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

Abstract

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 CF 3SO 3H as well as CF 3SO 3H–SbF 5 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.