Angewandte Chemie - International Edition, volume 58, issue 7, pages 1955-1959
Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity
Alexander Kreft
1
,
Alexander Lücht
1
,
J. Grunenberg
1
,
PA Peter B. Jones (2)
2
,
Daniel B. Werz
1
Publication type: Journal Article
Publication date: 2019-01-24
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 16.6
ISSN: 14337851, 15213773
General Chemistry
Catalysis
Abstract
The kinetics of (3+2) cycloaddition reactions of 18 different donor-acceptor cyclopropanes with the same aldehyde were studied by in situ NMR spectroscopy. Increasing the electron density of the donor residue accelerates the reaction by a factor of up to 50 compared to the standard system (donor group=phenyl), whereas electron-withdrawing substituents slow down the reaction by a factor up to 660. This behavior is in agreement with the Hammett substituent parameter σ. The obtained rate constants from the (3+2) cycloadditions correlate well with data from additionally studied (3+n) cycloadditions with a nitrone (n=3) and an isobenzofuran (n=4). A comparison of the kinetic data with the bond lengths in the cyclopropane (obtained by X-ray diffraction and computation), or the 1 H and 13 C NMR shifts, revealed no correlation. However, the computed relaxed force constants of donor-acceptor cyclopropanes proved to be a good indicator for the reactivity of the three-membered ring.
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Kreft A. et al. Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 7. pp. 1955-1959.
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Kreft A., Lücht A., Grunenberg J., Peter B. Jones (2) P., Werz D. B. Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity // Angewandte Chemie - International Edition. 2019. Vol. 58. No. 7. pp. 1955-1959.
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TY - JOUR
DO - 10.1002/anie.201812880
UR - https://doi.org/10.1002/anie.201812880
TI - Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity
T2 - Angewandte Chemie - International Edition
AU - Kreft, Alexander
AU - Lücht, Alexander
AU - Werz, Daniel B.
AU - Grunenberg, J.
AU - Peter B. Jones (2), PA
PY - 2019
DA - 2019/01/24 00:00:00
PB - Wiley
SP - 1955-1959
IS - 7
VL - 58
SN - 1433-7851
SN - 1521-3773
ER -
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@article{2019_Kreft,
author = {Alexander Kreft and Alexander Lücht and Daniel B. Werz and J. Grunenberg and PA Peter B. Jones (2)},
title = {Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity},
journal = {Angewandte Chemie - International Edition},
year = {2019},
volume = {58},
publisher = {Wiley},
month = {jan},
url = {https://doi.org/10.1002/anie.201812880},
number = {7},
pages = {1955--1959},
doi = {10.1002/anie.201812880}
}
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MLA
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Kreft, Alexander, et al. “Kinetic Studies of Donor-Acceptor Cyclopropanes: The Influence of Structural and Electronic Properties on the Reactivity.” Angewandte Chemie - International Edition, vol. 58, no. 7, Jan. 2019, pp. 1955-1959. https://doi.org/10.1002/anie.201812880.