Journal of the American Chemical Society, volume 144, issue 16, pages 7264-7282
Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities
Yaremenko Ivan A
1
,
Belyakova Yulia Yu
1
,
Radulov Peter S
1
,
Novikov Roman G.
1
,
Krivoshchapov Nikolai V
1, 2
,
Alabugin Igor V.
4
,
Publication type: Journal Article
Publication date: 2022-04-14
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 15
ISSN: 00027863, 15205126
General Chemistry
Catalysis
Biochemistry
Colloid and Surface Chemistry
Abstract
Stable tricyclic aminoperoxides can be selectively assembled via a catalyst-free three-component condensation of β,δ'-triketones, H2O2, and an NH-group source such as aqueous ammonia or ammonium salts. This procedure is scalable and can produce gram quantities of tricyclic heterocycles, containing peroxide, nitrogen, and oxygen cycles in one molecule. Amazingly, such complex tricyclic molecules are selectively formed despite the multitude of alternative reaction routes, via equilibration of peroxide, hemiaminal, monoperoxyacetal, and peroxyhemiaminal functionalities! The reaction is initiated by the "stereoelectronic frustration" of H2O2 and combines elements of thermodynamic and kinetic control with a variety of mono-, bi-, and tricyclic structures evolving under the conditions of thermodynamic control until they reach a kinetic wall created by the inverse α-effect, that is, the stereoelectronic penalty for the formation of peroxycarbenium ions and related transition states. Under these conditions, the reaction stops before reaching the most thermodynamically stable products at a stage where three different heterocycles are assembled and fused at the acyclic precursor frame.
Citations by journals
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1
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3
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Molecules
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3 publications, 17.65%
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Organic Letters
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2 publications, 11.76%
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2 publications, 11.76%
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Organometallics
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1 publication, 5.88%
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Journal of the American Chemical Society
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1 publication, 5.88%
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Catalysts
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1 publication, 5.88%
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Agrochemicals
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1 publication, 5.88%
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ACS In Focus
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1 publication, 5.88%
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1 publication, 5.88%
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1 publication, 5.88%
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1 publication, 5.88%
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1
2
3
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Citations by publishers
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1
2
3
4
5
6
7
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American Chemical Society (ACS)
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American Chemical Society (ACS)
7 publications, 41.18%
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Multidisciplinary Digital Publishing Institute (MDPI)
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Multidisciplinary Digital Publishing Institute (MDPI)
5 publications, 29.41%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
2 publications, 11.76%
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Wiley
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Wiley
2 publications, 11.76%
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Elsevier
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Elsevier
1 publication, 5.88%
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1
2
3
4
5
6
7
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- We do not take into account publications that 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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Yaremenko I. A. et al. Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities // Journal of the American Chemical Society. 2022. Vol. 144. No. 16. pp. 7264-7282.
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Yaremenko I. A., Belyakova Y. Yu., Radulov P. S., Novikov R. G., Medvedev M. G., Krivoshchapov N. V., Korlyukov A., Alabugin I. V., Terent'ev A. O. Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities // Journal of the American Chemical Society. 2022. Vol. 144. No. 16. pp. 7264-7282.
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TY - JOUR
DO - 10.1021/jacs.2c00406
UR - https://doi.org/10.1021%2Fjacs.2c00406
TI - Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities
T2 - Journal of the American Chemical Society
AU - Belyakova, Yulia Yu
AU - Krivoshchapov, Nikolai V
AU - Yaremenko, Ivan A
AU - Radulov, Peter S
AU - Novikov, Roman G.
AU - Medvedev, Michael G.
AU - Korlyukov, Alexander
AU - Alabugin, Igor V.
AU - Terent'ev, Alexander O.
PY - 2022
DA - 2022/04/14 00:00:00
PB - American Chemical Society (ACS)
SP - 7264-7282
IS - 16
VL - 144
SN - 0002-7863
SN - 1520-5126
ER -
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@article{2022_Yaremenko,
author = {Yulia Yu Belyakova and Nikolai V Krivoshchapov and Ivan A Yaremenko and Peter S Radulov and Roman G. Novikov and Michael G. Medvedev and Alexander Korlyukov and Igor V. Alabugin and Alexander O. Terent'ev},
title = {Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities},
journal = {Journal of the American Chemical Society},
year = {2022},
volume = {144},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Fjacs.2c00406},
number = {16},
pages = {7264--7282},
doi = {10.1021/jacs.2c00406}
}
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MLA
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Yaremenko, Ivan A., et al. “Inverse α-Effect as the Ariadne’s Thread on the Way to Tricyclic Aminoperoxides: Avoiding Thermodynamic Traps in the Labyrinth of Possibilities.” Journal of the American Chemical Society, vol. 144, no. 16, Apr. 2022, pp. 7264-7282. https://doi.org/10.1021%2Fjacs.2c00406.