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