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 CF 3SO 3H as well as CF 3SO 3H–SbF 5 superacidic media 5-amino...

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Bibliographic Details
Published in:Tetrahedron 2002-07, Vol.58 (27), p.5423-5426
Main Authors: Koltunov, Konstantin Yu, Surya Prakash, G.K, Rasul, Golam, Olah, George A
Format: Article
Language:English
Subjects:
aminonaphthol
condensation
ionic hydrogenation
superacid
superelectrophile
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Summary: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. Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(02)00512-4