Reactions of 5-, 6-, 7-, 8-Hydroxyquinolines and 5-Hydroxyisoquinoline with Benzene and Cyclohexane in Superacids | Sciact - CRIS-system of Boreskov Institute of Catalysis

Reactions of 5-, 6-, 7-, 8-Hydroxyquinolines and 5-Hydroxyisoquinoline with Benzene and Cyclohexane in Superacids Full article

Journal

Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904

Output data

Year: 2002, Volume: 67, Number: 12, Pages: 4330-4336 Pages count : 7 DOI: 10.1021/jo020099n

Tags

Aluminum; Chlorine; Hydrogenation; Ionic conduction

Authors

Koltunov Konstantin Yu. ¹ , Prakash G.K.Surya ¹ , Rasul Golam ¹ , Olah George A. ¹

Affiliations

1	Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, California 90089-1661

Isomeric 5-, 6-, 7-hydroxyquinolines (11−13) and 5-hydroxyisoquinoline (14) gave N,C-diprotonated dications in CF3SO3H−SbF5 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.

Koltunov K.Y. , Prakash G.K.S. , Rasul G. , Olah G.A.
Reactions of 5-, 6-, 7-, 8-Hydroxyquinolines and 5-Hydroxyisoquinoline with Benzene and Cyclohexane in Superacids
Journal of Organic Chemistry. 2002. V.67. N12. P.4330-4336. DOI: 10.1021/jo020099n WOS Scopus РИНЦ ANCAN OpenAlex

Submitted:	Feb 11, 2002
Published online:	May 11, 2002
Published print:	Jun 1, 2002

Web of science:	WOS:000176173700043
Scopus:	2-s2.0-0037077012
Elibrary:	14258993
Chemical Abstracts:	2002:354572
Chemical Abstracts (print):	137:93497
OpenAlex:	W1972826787

DB	Citing
Web of science	43
Scopus	46
OpenAlex	40