Document Detail

Superacidic activation of quinoline and isoquinoline; their reactions with cyclohexane and benzene(1).
MedLine Citation:
PMID:  17705536     Owner:  NLM     Status:  PubMed-not-MEDLINE    
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.
Konstantin Yu Koltunov; G K Surya Prakash; Golam Rasul; George A Olah
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Publication Detail:
Type:  Journal Article     Date:  2007-08-18
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  72     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2007 Sep 
Date Detail:
Created Date:  2007-09-07     Completed Date:  2007-10-16     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7394-7     Citation Subset:  -    
Loker Hydrocarbon Research Institute and Department of Chemistry, University of Southern California, University Park, Los Angeles, CA 90089-1661, USA.
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