Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles
Vitaly V Shorokhov
1
,
Vitaly Shorokhov
1
,
Beauty K. Chabuka
2
,
Timur P. Tikhonov
1
,
Anastasia V. Filippova
1
,
Sergey S Zhokhov
1
,
Victor A. Tafeenko
1
,
В. А. Тафеенко
1
,
Ivan A Andreev
3
,
Nina K Ratmanova
3
,
Maxim G Uchuskin
4
,
Igor V Trushkov
5
,
Igor V. Alabugin
2
,
Publication type: Journal Article
Publication date: 2024-09-12
scimago Q1
wos Q1
SJR: 1.235
CiteScore: 8.7
Impact factor: 5.0
ISSN: 15237060, 15237052
PubMed ID:
39265076
Abstract
Here, we present a new approach for the activation of donor–acceptor cyclopropanes in ring-opening reactions, which does not require the use of a Lewis or Brønsted acid as a catalyst. Donor–acceptor cyclopropanes containing a phenolic group as the donor undergo deprotonation and isomerization to form the corresponding quinone methides. This innovative strategy was applied to achieve (4 + 1)-annulation of cyclopropanes with sulfur ylides, affording functionalized dihydrobenzofurans. Additionally, the generated ortho- and para-(aza)quinone methides can be trapped by various CH-acids.
Found
Nothing found, try to update filter.
Found
Nothing found, try to update filter.
Top-30
Journals
|
1
2
|
|
|
Organic Letters
2 publications, 20%
|
|
|
Journal of Organic Chemistry
2 publications, 20%
|
|
|
Chemistry of Heterocyclic Compounds
1 publication, 10%
|
|
|
Angewandte Chemie - International Edition
1 publication, 10%
|
|
|
Angewandte Chemie
1 publication, 10%
|
|
|
Mendeleev Communications
1 publication, 10%
|
|
|
Organic Chemistry Frontiers
1 publication, 10%
|
|
|
Journal of the American Chemical Society
1 publication, 10%
|
|
|
1
2
|
Publishers
|
1
2
3
4
5
|
|
|
American Chemical Society (ACS)
5 publications, 50%
|
|
|
Wiley
2 publications, 20%
|
|
|
Springer Nature
1 publication, 10%
|
|
|
OOO Zhurnal "Mendeleevskie Soobshcheniya"
1 publication, 10%
|
|
|
Royal Society of Chemistry (RSC)
1 publication, 10%
|
|
|
1
2
3
4
5
|
- 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
10
Total citations:
10
Citations from 2025:
8
(80%)
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Shorokhov V. V. et al. Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles // Organic Letters. 2024. Vol. 26. No. 38. pp. 8177-8182.
GOST all authors (up to 50)
Copy
Shorokhov V. V., Shorokhov V., Chabuka B. K., Tikhonov T. P., Filippova A. V., Zhokhov S. S., Tafeenko V. A., Тафеенко В. А., Andreev I. A., Ratmanova N. K., Uchuskin M. G., Trushkov I. V., Alabugin I. V., Ivanova O. Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles // Organic Letters. 2024. Vol. 26. No. 38. pp. 8177-8182.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1021/acs.orglett.4c03106
UR - https://pubs.acs.org/doi/10.1021/acs.orglett.4c03106
TI - Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles
T2 - Organic Letters
AU - Shorokhov, Vitaly V
AU - Shorokhov, Vitaly
AU - Chabuka, Beauty K.
AU - Tikhonov, Timur P.
AU - Filippova, Anastasia V.
AU - Zhokhov, Sergey S
AU - Tafeenko, Victor A.
AU - Тафеенко, В. А.
AU - Andreev, Ivan A
AU - Ratmanova, Nina K
AU - Uchuskin, Maxim G
AU - Trushkov, Igor V
AU - Alabugin, Igor V.
AU - Ivanova, Olga
PY - 2024
DA - 2024/09/12
PB - American Chemical Society (ACS)
SP - 8177-8182
IS - 38
VL - 26
PMID - 39265076
SN - 1523-7060
SN - 1523-7052
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2024_Shorokhov,
author = {Vitaly V Shorokhov and Vitaly Shorokhov and Beauty K. Chabuka and Timur P. Tikhonov and Anastasia V. Filippova and Sergey S Zhokhov and Victor A. Tafeenko and В. А. Тафеенко and Ivan A Andreev and Nina K Ratmanova and Maxim G Uchuskin and Igor V Trushkov and Igor V. Alabugin and Olga Ivanova},
title = {Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles},
journal = {Organic Letters},
year = {2024},
volume = {26},
publisher = {American Chemical Society (ACS)},
month = {sep},
url = {https://pubs.acs.org/doi/10.1021/acs.orglett.4c03106},
number = {38},
pages = {8177--8182},
doi = {10.1021/acs.orglett.4c03106}
}
Cite this
MLA
Copy
Shorokhov, Vitaly V., et al. “Converting Strain Release into Aromaticity Loss for Activation of Donor–Acceptor Cyclopropanes: Generation of Quinone Methide Traps for C-Nucleophiles.” Organic Letters, vol. 26, no. 38, Sep. 2024, pp. 8177-8182. https://pubs.acs.org/doi/10.1021/acs.orglett.4c03106.