Superacidic Activation of Quinoline and Isoquinoline; Their Reactions with Cyclohexane and Benzene Full article
| Journal |
Journal of Organic Chemistry
ISSN: 0022-3263 , E-ISSN: 1520-6904 |
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| Output data | Year: 2007, Volume: 72, Number: 19, Pages: 7394-7397 Pages count : 4 DOI: 10.1021/jo070875x | ||||||
| Tags | Acidity; Chemical activation; Derivatives; Hydrogenation; Nucleophiles; Reaction kinetics | ||||||
| Authors |
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| Affiliations |
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Funding (1)
| 1 | National Science Foundation |
Abstract:
Quinoline (1) and isoquinoline (2), upon activation by strong acids, lead to intermediate N,C-diprotonated dications, which are involved in reactions with weak nucleophiles. Thus, 1 and 2 undergo selective ionic hydrogenation with cyclohexane in CF3SO3H−SbF5, HBr−AlBr3−CH2Br2, or HCl−AlCl3−CH2Cl2 acid systems to give their 5,6,7,8-tetrahydro derivatives. They also readily condense with benzene in the presence of HBr−AlBr3 or HCl−AlCl3 to provide 5,6,7,8-tetrahydro-5,7-diphenylquinoline (10) and 5,6,7,8-tetrahydro-6,8-diphenylisoquinoline (12), respectively.
Cite:
Koltunov K.Y.
, Prakash G.K.S.
, Rasul G.
, Olah G.A.
Superacidic Activation of Quinoline and Isoquinoline; Their Reactions with Cyclohexane and Benzene
Journal of Organic Chemistry. 2007. V.72. N19. P.7394-7397. DOI: 10.1021/jo070875x WOS Scopus РИНЦ ANCAN OpenAlex
Superacidic Activation of Quinoline and Isoquinoline; Their Reactions with Cyclohexane and Benzene
Journal of Organic Chemistry. 2007. V.72. N19. P.7394-7397. DOI: 10.1021/jo070875x WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
| Submitted: | May 12, 2007 |
| Published online: | Aug 18, 2007 |
| Published print: | Sep 1, 2007 |
Identifiers:
| Web of science: | WOS:000249371200042 |
| Scopus: | 2-s2.0-34548708458 |
| Elibrary: | 13538339 |
| Chemical Abstracts: | 2007:921136 |
| Chemical Abstracts (print): | 147:448321 |
| OpenAlex: | W1971568255 |