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
Q1
Q1
SJR: 5.300
CiteScore: 26.6
Impact factor: 16.1
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.
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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.
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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
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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
PB - Wiley
SP - 3187-3191
IS - 12
VL - 53
SN - 1433-7851
SN - 1521-3773
ER -
Cite this
BibTex (up to 50 authors)
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@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.