, volume 67 , issue 12 , pages 4330-4336

Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids.

Konstantin Yu Koltunov ¹

G. Vijaya Prakash ¹

Golam Rasul ¹

George Olah ¹

Hide authors affiliations Show authors affiliations: 1 affiliation

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

Publication type: Journal Article

Publication date: 2002-05-11

American Chemical Society (ACS)

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR: 0.737

CiteScore: 6.1

Impact factor: 3.6

ISSN: 00223263, 15206904

DOI: 10.1021/jo020099n

Copy DOI

PubMed ID: 12054971

Organic Chemistry

Abstract

Isomeric 5-, 6-, 7-hydroxyquinolines (11-13) and 5-hydroxyisoquinoline (14) gave N,C-diprotonated dications in CF(3)SO(3)H-SbF(5) 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.

Found

1 citation

Ryabukhin Dmitry

PhD in Chemistry

56 publications, 848 citations

h-index: 13

Saint-Petersburg State Forest Technical University

V. M. Gorbatov Federal Research Center for Food Systems of Russian Academy of Sciences

Top-30

Journals

	1 2 3 4 5 6
Tetrahedron Letters	Tetrahedron Letters, 6, 16.67% Tetrahedron Letters 6 publications, 16.67%
Journal of Organic Chemistry	Journal of Organic Chemistry, 4, 11.11% Journal of Organic Chemistry 4 publications, 11.11%
Tetrahedron	Tetrahedron, 3, 8.33% Tetrahedron 3 publications, 8.33%
Mendeleev Communications	Mendeleev Communications, 3, 8.33% Mendeleev Communications 3 publications, 8.33%
Chemistry - A European Journal	Chemistry - A European Journal, 2, 5.56% Chemistry - A European Journal 2 publications, 5.56%
Organic and Biomolecular Chemistry	Organic and Biomolecular Chemistry, 2, 5.56% Organic and Biomolecular Chemistry 2 publications, 5.56%
Chemistry of Heterocyclic Compounds	Chemistry of Heterocyclic Compounds, 1, 2.78% Chemistry of Heterocyclic Compounds 1 publication, 2.78%
Chemical and Pharmaceutical Bulletin	Chemical and Pharmaceutical Bulletin, 1, 2.78% Chemical and Pharmaceutical Bulletin 1 publication, 2.78%
Journal of the Electrochemical Society	Journal of the Electrochemical Society, 1, 2.78% Journal of the Electrochemical Society 1 publication, 2.78%
Catalysis Letters	Catalysis Letters, 1, 2.78% Catalysis Letters 1 publication, 2.78%
Journal of Structural Chemistry	Journal of Structural Chemistry, 1, 2.78% Journal of Structural Chemistry 1 publication, 2.78%
Journal of Molecular Catalysis A Chemical	Journal of Molecular Catalysis A Chemical, 1, 2.78% Journal of Molecular Catalysis A Chemical 1 publication, 2.78%
European Journal of Organic Chemistry	European Journal of Organic Chemistry, 1, 2.78% European Journal of Organic Chemistry 1 publication, 2.78%
Organic Letters	Organic Letters, 1, 2.78% Organic Letters 1 publication, 2.78%
Journal of the American Chemical Society	Journal of the American Chemical Society, 1, 2.78% Journal of the American Chemical Society 1 publication, 2.78%
Chemical Communications	Chemical Communications, 1, 2.78% Chemical Communications 1 publication, 2.78%
Chemical Society Reviews	Chemical Society Reviews, 1, 2.78% Chemical Society Reviews 1 publication, 2.78%
Russian Journal of Organic Chemistry	Russian Journal of Organic Chemistry, 1, 2.78% Russian Journal of Organic Chemistry 1 publication, 2.78%
Science	Science, 1, 2.78% Science 1 publication, 2.78%
Heterocycles	Heterocycles, 1, 2.78% Heterocycles 1 publication, 2.78%
Accounts of Chemical Research	Accounts of Chemical Research, 1, 2.78% Accounts of Chemical Research 1 publication, 2.78%
	1 2 3 4 5 6

Publishers

	2 4 6 8 10 12 14
Elsevier	Elsevier, 13, 36.11% Elsevier 13 publications, 36.11%
American Chemical Society (ACS)	American Chemical Society (ACS), 7, 19.44% American Chemical Society (ACS) 7 publications, 19.44%
Royal Society of Chemistry (RSC)	Royal Society of Chemistry (RSC), 4, 11.11% Royal Society of Chemistry (RSC) 4 publications, 11.11%
Wiley	Wiley, 3, 8.33% Wiley 3 publications, 8.33%
Springer Nature	Springer Nature, 2, 5.56% Springer Nature 2 publications, 5.56%
Pleiades Publishing	Pleiades Publishing, 2, 5.56% Pleiades Publishing 2 publications, 5.56%
Pharmaceutical Society of Japan	Pharmaceutical Society of Japan, 1, 2.78% Pharmaceutical Society of Japan 1 publication, 2.78%
The Electrochemical Society	The Electrochemical Society, 1, 2.78% The Electrochemical Society 1 publication, 2.78%
American Association for the Advancement of Science (AAAS)	American Association for the Advancement of Science (AAAS), 1, 2.78% American Association for the Advancement of Science (AAAS) 1 publication, 2.78%
The Japan Institute of Heterocyclic Chemistry	The Japan Institute of Heterocyclic Chemistry, 1, 2.78% The Japan Institute of Heterocyclic Chemistry 1 publication, 2.78%
	2 4 6 8 10 12 14

We do not take into account publications without a DOI.
Statistics recalculated weekly.

Are you a researcher?

Create a profile to get free access to personal recommendations for colleagues and new articles.

Metrics

Cite this

GOST |

Cite this

GOST Copy

Koltunov K. Yu. et al. Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids. // Journal of Organic Chemistry. 2002. Vol. 67. No. 12. pp. 4330-4336.

GOST all authors (up to 50) Copy

Koltunov K. Yu., Vijaya Prakash G., Rasul G., Olah G. Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids. // Journal of Organic Chemistry. 2002. Vol. 67. No. 12. pp. 4330-4336.

RIS |

Cite this

RIS Copy

TY - JOUR

DO - 10.1021/jo020099n

UR - https://doi.org/10.1021/jo020099n

TI - Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids.

T2 - Journal of Organic Chemistry

AU - Koltunov, Konstantin Yu

AU - Vijaya Prakash, G.

AU - Rasul, Golam

AU - Olah, George

PY - 2002

DA - 2002/05/11

PB - American Chemical Society (ACS)

SP - 4330-4336

IS - 12

VL - 67

PMID - 12054971

SN - 0022-3263

SN - 1520-6904

ER -

BibTex |

Cite this

BibTex (up to 50 authors) Copy

@article{2002_Koltunov,

author = {Konstantin Yu Koltunov and G. Vijaya Prakash and Golam Rasul and George Olah},

title = {Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids.},

journal = {Journal of Organic Chemistry},

year = {2002},

volume = {67},

publisher = {American Chemical Society (ACS)},

month = {may},

url = {https://doi.org/10.1021/jo020099n},

number = {12},

pages = {4330--4336},

doi = {10.1021/jo020099n}

}

MLA

Cite this

MLA Copy

Koltunov, Konstantin Yu., et al. “Reactions of 5-, 6-, 7-, 8-hydroxyquinolines and 5-hydroxyisoquinoline with benzene and cyclohexane in superacids..” Journal of Organic Chemistry, vol. 67, no. 12, May. 2002, pp. 4330-4336. https://doi.org/10.1021/jo020099n.

Publisher

American Chemical Society (ACS)

Journal

Journal of Organic Chemistry

scimago Q2

wos Q1

SJR

0.737

CiteScore

6.1

Impact factor

3.6

ISSN

00223263 (Print)

15206904 (Electronic)