Angewandte Chemie - International Edition, volume 53, issue 12, pages 3187-3191
A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles
Publication type: Journal Article
Publication date: 2014-02-19
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
A new type of donor-acceptor cyclopropane reactivity has been discovered. On treatment with anhydrous GaCl3 , they react as sources of even-numbered 1,2- and 1,4-dipoles instead of the classical odd-numbered 1,3-dipoles due to migration of positive charge from the benzyl center. This type of reactivity has been demonstrated for new reactions, namely, cyclodimerizations of donor-acceptor cyclopropanes that occur as [2+2]-, [3+2]-, [4+2]-, [5+2], [4+3]-, and [5+4]-annulations. The [4+2]-annulation of 2-arylcyclopropane-1,1-dicarboxylates to give polysubstituted 2-aryltetralins has been developed in a preparative version that provides exceedingly high regio- and diastereoselectivity and high yields. The strategy for selective hetero-combination of donor-acceptor cyclopropanes was also been developed. The mechanisms of the discovered reactions involving the formation of a comparatively stable 1,2-ylide intermediate have been studied.
Top-30
Citations by journals
|
2
4
6
8
10
12
14
16
18
|
|
|
Journal of Organic Chemistry
17 publications, 14.66%
|
|
|
Organic Letters
14 publications, 12.07%
|
|
|
Angewandte Chemie - International Edition
9 publications, 7.76%
|
|
|
Angewandte Chemie
9 publications, 7.76%
|
|
|
Chemistry - A European Journal
6 publications, 5.17%
|
|
|
Russian Chemical Bulletin
6 publications, 5.17%
|
|
|
European Journal of Organic Chemistry
6 publications, 5.17%
|
|
|
Organic and Biomolecular Chemistry
5 publications, 4.31%
|
|
|
Mendeleev Communications
4 publications, 3.45%
|
|
|
Tetrahedron Letters
4 publications, 3.45%
|
|
|
Chemical Communications
4 publications, 3.45%
|
|
|
Synlett
3 publications, 2.59%
|
|
|
Organometallics
2 publications, 1.72%
|
|
|
MolBank
2 publications, 1.72%
|
|
|
Molecules
2 publications, 1.72%
|
|
|
Russian Chemical Reviews
2 publications, 1.72%
|
|
|
Advanced Synthesis and Catalysis
2 publications, 1.72%
|
|
|
Journal of the American Chemical Society
2 publications, 1.72%
|
|
|
Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
1 publication, 0.86%
|
|
|
Science China Chemistry
1 publication, 0.86%
|
|
|
Journal of Molecular Structure
1 publication, 0.86%
|
|
|
Helvetica Chimica Acta
1 publication, 0.86%
|
|
|
Israel Journal of Chemistry
1 publication, 0.86%
|
|
|
ChemistrySelect
1 publication, 0.86%
|
|
|
Asian Journal of Organic Chemistry
1 publication, 0.86%
|
|
|
ChemInform
1 publication, 0.86%
|
|
|
Inorganic Chemistry
1 publication, 0.86%
|
|
|
Chinese Journal of Organic Chemistry
1 publication, 0.86%
|
|
|
RSC Advances
1 publication, 0.86%
|
|
|
Organic Chemistry Frontiers
1 publication, 0.86%
|
|
|
2
4
6
8
10
12
14
16
18
|
Citations by publishers
|
5
10
15
20
25
30
35
40
|
|
|
Wiley
39 publications, 33.62%
|
|
|
American Chemical Society (ACS)
36 publications, 31.03%
|
|
|
Royal Society of Chemistry (RSC)
11 publications, 9.48%
|
|
|
Elsevier
10 publications, 8.62%
|
|
|
Springer Nature
8 publications, 6.9%
|
|
|
Multidisciplinary Digital Publishing Institute (MDPI)
4 publications, 3.45%
|
|
|
Thieme
3 publications, 2.59%
|
|
|
Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii
2 publications, 1.72%
|
|
|
Society of Synthetic Organic Chemistry
1 publication, 0.86%
|
|
|
Shanghai Institute of Organic Chemistry
1 publication, 0.86%
|
|
|
American Institute of Physics (AIP)
1 publication, 0.86%
|
|
|
5
10
15
20
25
30
35
40
|
- 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.
{"yearsCitations":{"type":"bar","data":{"show":true,"labels":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[0,0,0,0,0,0,0,0,0,0,0],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["","","","","","","","","","",""],"datasets":[{"label":"Citations number","data":[4,15,16,17,13,14,6,10,7,6,8],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":["3.45","12.93","13.79","14.66","11.21","12.07","5.17","8.62","6.03","5.17","6.9"],"barThickness":null}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"journals":{"type":"bar","data":{"show":true,"labels":["Journal of Organic Chemistry","Organic Letters","Angewandte Chemie - International Edition","Angewandte Chemie","Chemistry - A European Journal","Russian Chemical Bulletin","European Journal of Organic Chemistry","Organic and Biomolecular Chemistry","Mendeleev Communications","Tetrahedron Letters","Chemical Communications","Synlett","Organometallics","MolBank","Molecules","Russian Chemical Reviews","Advanced Synthesis and Catalysis","Journal of the American Chemical Society","Yuki Gosei Kagaku Kyokaishi\/Journal of Synthetic Organic Chemistry","Science China Chemistry","Journal of Molecular Structure","Helvetica Chimica Acta","Israel Journal of Chemistry","ChemistrySelect","Asian Journal of Organic Chemistry","ChemInform","Inorganic Chemistry","Chinese Journal of Organic Chemistry","RSC Advances","Organic Chemistry Frontiers"],"ids":[8697,3315,19215,25450,24708,10918,19472,541,5294,6133,9073,10217,1409,20017,1770,23802,3906,4813,3551,14409,9347,32,17699,8021,9409,25372,24714,11696,3100,3991],"codes":[0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/QzzkQMUwda0fYU3txrAv3z24JfXJEjptEQpWMERc_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/6EJSsoiR4fNMNMPFBpMh5yKuYKcPXJDQKvKVeEMy_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp"],"datasets":[{"label":"","data":[17,14,9,9,6,6,6,5,4,4,4,3,2,2,2,2,2,2,1,1,1,1,1,1,1,1,1,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[14.66,12.07,7.76,7.76,5.17,5.17,5.17,4.31,3.45,3.45,3.45,2.59,1.72,1.72,1.72,1.72,1.72,1.72,0.86,0.86,0.86,0.86,0.86,0.86,0.86,0.86,0.86,0.86,0.86,0.86],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Journals","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"publishers":{"type":"bar","data":{"show":true,"labels":["Wiley","American Chemical Society (ACS)","Royal Society of Chemistry (RSC)","Elsevier","Springer Nature","Multidisciplinary Digital Publishing Institute (MDPI)","Thieme","Autonomous Non-profit Organization Editorial Board of the journal Uspekhi Khimii","Society of Synthetic Organic Chemistry","Shanghai Institute of Organic Chemistry","American Institute of Physics (AIP)"],"ids":[11,40,123,17,8,202,135,9422,1303,8960,250],"codes":[0,0,0,0,0,0,0,0,0,0,0],"imageUrls":["\/storage\/images\/resized\/bRyGpdm98BkAUYiK1YFNpl5Z7hPu6Gd87gbIeuG3_medium.webp","\/storage\/images\/resized\/iLiQsFqFaSEx6chlGQ5fbAwF6VYU3WWa08hkss0g_medium.webp","\/storage\/images\/resized\/leiAYcRDGTSl5B1eCnwpSGqmDEUEfDPPoYisFGhT_medium.webp","\/storage\/images\/resized\/GDnYOu1UpMMfMMRV6Aqle4H0YLLsraeD9IP9qScG_medium.webp","\/storage\/images\/resized\/voXLqlsvTwv5p3iMQ8Dhs95nqB4AXOG7Taj7G4ra_medium.webp","\/storage\/images\/resized\/MjH1ITP7lMYGxeqUZfkt2BnVLgjkk413jwBV97XX_medium.webp","\/storage\/images\/resized\/xqixcltwJYe6H8Uco2JbAFfIOzt7UNKH0OcPOPzO_medium.webp","\/storage\/images\/resized\/9Mus3KG1Tkd7Bwaurt8H3RwWh0CxRlGoO6ng9UK1_medium.webp","\/storage\/images\/resized\/QzzkQMUwda0fYU3txrAv3z24JfXJEjptEQpWMERc_medium.webp","\/storage\/images\/resized\/6EJSsoiR4fNMNMPFBpMh5yKuYKcPXJDQKvKVeEMy_medium.webp","\/storage\/images\/resized\/ARM4e6URKRsbRZvIF0vFis9DjxGloBjnBYJXbHmZ_medium.webp"],"datasets":[{"label":"","data":[39,36,11,10,8,4,3,2,1,1,1],"backgroundColor":["#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6","#3B82F6"],"percentage":[33.62,31.03,9.48,8.62,6.9,3.45,2.59,1.72,0.86,0.86,0.86],"barThickness":13}]},"options":{"indexAxis":"y","maintainAspectRatio":false,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false},"x":{"ticks":{"stepSize":null,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":false}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Publishers","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartiles":{"type":"bar","data":{"show":true,"labels":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,1,0,0,0,1,0,0,1,0],"percentage":["0","0","0.86","0","0","0","0.86","0","0","0.86","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[1,2,2,2,1,2,1,1,0,2,2],"percentage":["0.86","1.72","1.72","1.72","0.86","1.72","0.86","0.86","0","1.72","1.72"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[1,3,2,3,0,4,0,0,1,1,0],"percentage":["0.86","2.59","1.72","2.59","0","3.45","0","0","0.86","0.86","0"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,10,11,11,12,8,3,9,6,2,6],"percentage":["0.86","8.62","9.48","9.48","10.34","6.9","2.59","7.76","5.17","1.72","5.17"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,0,0,1,0,0,1,0,0,0,0],"percentage":["0.86","0","0","0.86","0","0","0.86","0","0","0","0"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by SCImago per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}},"yearsCitationsQuartilesWs":{"type":"bar","data":{"show":true,"labels":[2014,2015,2016,2017,2018,2019,2020,2021,2022,2023,2024],"ids":[],"codes":[],"imageUrls":[],"datasets":[{"label":"Q4","backgroundColor":"rgb(221,90,78)","data":[0,0,1,0,0,0,0,0,0,0,0],"percentage":["0","0","0.86","0","0","0","0","0","0","0","0"]},{"label":"Q3","backgroundColor":"rgb(251, 163,83)","data":[2,3,4,3,1,2,1,1,0,2,1],"percentage":["1.72","2.59","3.45","2.59","0.86","1.72","0.86","0.86","0","1.72","0.86"]},{"label":"Q2","backgroundColor":"rgb(232, 213, 89)","data":[0,7,4,3,2,4,1,2,5,1,2],"percentage":["0","6.03","3.45","2.59","1.72","3.45","0.86","1.72","4.31","0.86","1.72"]},{"label":"Q1","backgroundColor":"rgb(164, 207, 99)","data":[1,4,6,8,9,6,2,6,2,2,4],"percentage":["0.86","3.45","5.17","6.9","7.76","5.17","1.72","5.17","1.72","1.72","3.45"]},{"label":"Quartile not defined","backgroundColor":"#E5E7EB","data":[1,1,1,3,1,2,2,1,0,1,1],"percentage":["0.86","0.86","0.86","2.59","0.86","1.72","1.72","0.86","0","0.86","0.86"]}]},"options":{"indexAxis":"x","maintainAspectRatio":true,"scales":{"y":{"ticks":{"precision":0,"autoSkip":false,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true},"x":{"ticks":{"stepSize":1,"precision":0,"font":{"family":"Montserrat"},"color":"#000000"},"stacked":true}},"plugins":{"legend":{"position":"top","labels":{"font":{"family":"Montserrat"},"color":"#000000"}},"title":{"display":true,"text":"Citations quartiles by WoS per year","font":{"size":24,"family":"Montserrat","weight":600},"color":"#000000"}}}}}
Are you a researcher?
Create a profile to get free access to personal recommendations for colleagues and new articles.
Metrics
Cite this
GOST |
RIS |
BibTex |
MLA
Cite this
GOST
Copy
Novikov R. G. et al. A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles // Angewandte Chemie - International Edition. 2014. Vol. 53. No. 12. pp. 3187-3191.
GOST all authors (up to 50)
Copy
Novikov R. G., Tarasova A. V., Korolev V. A., Timofeev V. P., Tomilov Y. V. A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles // Angewandte Chemie - International Edition. 2014. Vol. 53. No. 12. pp. 3187-3191.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1002/anie.201306186
UR - https://doi.org/10.1002/anie.201306186
TI - A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles
T2 - Angewandte Chemie - International Edition
AU - Novikov, Roman G.
AU - Tarasova, Anna V
AU - Korolev, Victor A
AU - Timofeev, Vladimir P
AU - Tomilov, Yury V.
PY - 2014
DA - 2014/02/19 00:00:00
PB - Wiley
SP - 3187-3191
IS - 12
VL - 53
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex
Copy
@article{2014_Novikov,
author = {Roman G. Novikov and Anna V Tarasova and Victor A Korolev and Vladimir P Timofeev and Yury V. Tomilov},
title = {A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles},
journal = {Angewandte Chemie - International Edition},
year = {2014},
volume = {53},
publisher = {Wiley},
month = {feb},
url = {https://doi.org/10.1002/anie.201306186},
number = {12},
pages = {3187--3191},
doi = {10.1002/anie.201306186}
}
Cite this
MLA
Copy
Novikov, Roman G., et al. “A New Type of Donor-Acceptor Cyclopropane Reactivity: The Generation of Formal 1,2- and 1,4-Dipoles.” Angewandte Chemie - International Edition, vol. 53, no. 12, Feb. 2014, pp. 3187-3191. https://doi.org/10.1002/anie.201306186.