Chemistry - A European Journal, volume 15, issue 35, pages 8852-8860
Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations
Publication type: Journal Article
Publication date: 2009-09-07
Journal:
Chemistry - A European Journal
Quartile SCImago
Q1
Quartile WOS
Q2
Impact factor: 4.3
ISSN: 09476539, 15213765
General Chemistry
Catalysis
Organic Chemistry
Abstract
Diarylvinylidenecyclopropanes undergo a novel rearrangement in the presence of the Brønsted acid Tf(2)NH (Tf: trifluoromethanesulfonyl) to give the corresponding naphthalene derivatives in good to high yields upon heating, whereas in the presence of the Brønsted acid toluene-4-sulfonic acid (p-TSA), the corresponding triene derivatives are afforded in moderate to good yields under mild conditions. Corresponding mechanistic studies on the basis of density functional theory (DFT) with the Gaussian03 program by using the B3LYP method have revealed that the pK(a) value of the Brønsted acid, as well as the entropy and solvent effects, plays a significant role in this reaction; these factors can discriminate the differences in the reactivity and regioselectivity among the Brønsted acids used in this reaction. In the presence of Lewis acid Sn(OTf)(2), a butatrienecyclopane can produce the corresponding ring-opened products in moderate yields.
Top-30
Citations by journals
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Angewandte Chemie - International Edition
4 publications, 15.38%
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Angewandte Chemie
4 publications, 15.38%
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Chemistry - A European Journal
4 publications, 15.38%
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Journal of Organic Chemistry
2 publications, 7.69%
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Organic Reaction Mechanisms
2 publications, 7.69%
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European Journal of Organic Chemistry
1 publication, 3.85%
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Tetrahedron Letters
1 publication, 3.85%
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Tetrahedron
1 publication, 3.85%
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Journal of Organometallic Chemistry
1 publication, 3.85%
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ChemInform
1 publication, 3.85%
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Chemical Reviews
1 publication, 3.85%
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Organic Letters
1 publication, 3.85%
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SpringerBriefs in Molecular Science
1 publication, 3.85%
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Russian Chemical Reviews
1 publication, 3.85%
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Citations by publishers
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16
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Wiley
16 publications, 61.54%
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American Chemical Society (ACS)
4 publications, 15.38%
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Elsevier
3 publications, 11.54%
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Springer Nature
1 publication, 3.85%
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Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
1 publication, 3.85%
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- We do not take into account publications without a DOI.
- Statistics recalculated only for publications connected to researchers, organizations and labs registered on the platform.
- Statistics recalculated weekly.
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Li W., Shi M., Li Y. Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations // Chemistry - A European Journal. 2009. Vol. 15. No. 35. pp. 8852-8860.
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Li W., Shi M., Li Y. Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations // Chemistry - A European Journal. 2009. Vol. 15. No. 35. pp. 8852-8860.
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TY - JOUR
DO - 10.1002/chem.200901172
UR - https://doi.org/10.1002/chem.200901172
TI - Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations
T2 - Chemistry - A European Journal
AU - Li, Wei
AU - Shi, Min
AU - Li, Yuxue
PY - 2009
DA - 2009/09/07 00:00:00
PB - Wiley
SP - 8852-8860
IS - 35
VL - 15
SN - 0947-6539
SN - 1521-3765
ER -
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@article{2009_Li,
author = {Wei Li and Min Shi and Yuxue Li},
title = {Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations},
journal = {Chemistry - A European Journal},
year = {2009},
volume = {15},
publisher = {Wiley},
month = {sep},
url = {https://doi.org/10.1002/chem.200901172},
number = {35},
pages = {8852--8860},
doi = {10.1002/chem.200901172}
}
Cite this
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Li, Wei, et al. “Brønsted Acid Mediated Novel Rearrangements of Diarylvinylidenecyclopropanes and Mechanistic Investigations Based on DFT Calculations.” Chemistry - A European Journal, vol. 15, no. 35, Sep. 2009, pp. 8852-8860. https://doi.org/10.1002/chem.200901172.