Journal of Organic Chemistry, volume 72, issue 2, pages 509-516
Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups
Publication type: Journal Article
Publication date: 2006-12-15
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
Lewis-acid-catalyzed reactions of arylvinylidenecyclopropanes having three substituents at the corresponding cyclopropyl rings have been investigated thoroughly. The reaction products are highly dependent on the substituents at the corresponding cyclopropyl rings and the electronic nature of the aryl groups. For arylvinylidenecyclopropanes bearing two alkyl groups at the C-1 position (R1, R2, R3=aryl; R4=H; R5, R6=alkyl), naphthalene derivatives were formed in the presence of Lewis-acid Eu(OTf)3 in DCE at 40 degrees C. For arylvinylidenecyclopropanes in which R1, R2, R3=aryl and R4, R5=alkyl (syn/anti isomeric mixtures), the corresponding 6aH-benzo[c]fluorine derivatives were formed in the syn-configuration via a double intramolecular Friedel-Crafts reaction when all of the aryl groups do not have electron-withdrawing groups or the corresponding indene derivatives were obtained via an intramolecular Friedel-Crafts reaction as long as one electron-deficient aryl group was attached. For arylvinylidenecyclopropanes in which R1, R2, R3, R4=aryl and R5=alkyl or H, the corresponding indene derivatives were obtained exclusively via a sterically demanding intramolecular Friedel-Crafts reaction. Lewis-acid effects and mechanistic insights have been discussed on the basis of experimental investigations.
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Citations by publishers
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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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Zhang Y. et al. Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups // Journal of Organic Chemistry. 2006. Vol. 72. No. 2. pp. 509-516.
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Zhang Y., Lu J., Xu G. C., Shi M. Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups // Journal of Organic Chemistry. 2006. Vol. 72. No. 2. pp. 509-516.
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TY - JOUR
DO - 10.1021/jo061899r
UR - https://doi.org/10.1021/jo061899r
TI - Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups
T2 - Journal of Organic Chemistry
AU - Zhang, Yun-peng
AU - Lu, Jian-Mei
AU - Xu, Guang Cai
AU - Shi, Min
PY - 2006
DA - 2006/12/15 00:00:00
PB - American Chemical Society (ACS)
SP - 509-516
IS - 2
VL - 72
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2006_Zhang,
author = {Yun-peng Zhang and Jian-Mei Lu and Guang Cai Xu and Min Shi},
title = {Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups},
journal = {Journal of Organic Chemistry},
year = {2006},
volume = {72},
publisher = {American Chemical Society (ACS)},
month = {dec},
url = {https://doi.org/10.1021/jo061899r},
number = {2},
pages = {509--516},
doi = {10.1021/jo061899r}
}
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MLA
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Zhang, Yun-peng, et al. “Lewis-Acid-Catalyzed Rearrangement of Arylvinylidenecyclopropanes: Significant Influence of Substituents and Electronic Nature of Aryl Groups.” Journal of Organic Chemistry, vol. 72, no. 2, Dec. 2006, pp. 509-516. https://doi.org/10.1021/jo061899r.