Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles
Publication type: Journal Article
Publication date: 2002-12-29
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
Abstract
According to the 1H and 1 3C NMR data, 5-azonia-4-hydroxynaphthalen-1-onium cation, generated by protonation of 8-hydroxyquinoline in the system CF3SO3H-SbF5, reacts with cyclohexane to give diprotonated 5,6,7,8-tetrahydroquinolin-8-one. Further reaction of the latter with cyclohexane yields 5,6,7,8-tetrahydroquinolinium ion. The reaction of 8-hydroxyquinoline with benzene in the presence of aluminum bromide or chloride gives 6-phenyl-5,6,7,8-tetrahydroquinolin-8-one and product of its intramolecular cyclization, 11-hydroxy-6,11-dihydro-6,11-methano-5H-benzo[5,6]cyclohepta[1,2-b]pyridine. The effect of the protonated nitrogen atom on the electrophilicity of dications is discussed.
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Koltunov K. Y., Repinskaya I. B. Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 3. pp. 437-442.
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Koltunov K. Y., Repinskaya I. B. Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles // Russian Journal of Organic Chemistry. 2002. Vol. 38. No. 3. pp. 437-442.
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RIS
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TY - JOUR
DO - 10.1023/a:1016306814374
UR - https://doi.org/10.1023/a:1016306814374
TI - Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles
T2 - Russian Journal of Organic Chemistry
AU - Koltunov, K. Yu.
AU - Repinskaya, I B
PY - 2002
DA - 2002/12/29
PB - Pleiades Publishing
SP - 437-442
IS - 3
VL - 38
SN - 1070-4280
SN - 1608-3393
ER -
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BibTex (up to 50 authors)
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@article{2002_Koltunov,
author = {K. Yu. Koltunov and I B Repinskaya},
title = {Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles},
journal = {Russian Journal of Organic Chemistry},
year = {2002},
volume = {38},
publisher = {Pleiades Publishing},
month = {dec},
url = {https://doi.org/10.1023/a:1016306814374},
number = {3},
pages = {437--442},
doi = {10.1023/a:1016306814374}
}
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MLA
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Koltunov, K. Yu., and I B Repinskaya. “Superelectrophilic Activation of 8-Hydroxyquinoline in Acid Media and Its Reactions with Weak Nucleophiles.” Russian Journal of Organic Chemistry, vol. 38, no. 3, Dec. 2002, pp. 437-442. https://doi.org/10.1023/a:1016306814374.