Journal of Organic Chemistry, volume 83, issue 8, pages 4840-4850
Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes.
Publication type: Journal Article
Publication date: 2018-04-04
Journal:
Journal of Organic Chemistry
Quartile SCImago
Q1
Quartile WOS
Q1
Impact factor: 3.6
ISSN: 00223263, 15206904
Organic Chemistry
Abstract
A rare example of chemospecificity in the tandem Diels-Alder reaction of activated alkynes and bis-dienes has been revealed. The reaction between bis-furyl dienes and DMAD occurs at 25-80 °C and leads to kinetically controlled "pincer" adducts, 4a,8a-disubstituted 1,4:5,8-diepoxynaphthalenes. On the contrary, only thermodynamically controlled "domino" adducts (2,3-disubstituted 1,4:5,8-diepoxynaphthalenes) are formed in the same reaction at 140 °C. The "pincer" adducts can be transformed to the "domino" adducts at heating. The rate constants for reactions of both types were calculated using dynamic 1H NMR spectroscopy.
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Citations by publishers
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- We do not take into account publications that without a DOI.
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- Statistics recalculated weekly.
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Borisova K. K. et al. Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes. // Journal of Organic Chemistry. 2018. Vol. 83. No. 8. pp. 4840-4850.
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Borisova K. K., Kvyatkovskaya E. A., Nikitina E. V., Aysin R., Novikov R. G., Zubkov F. I. Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes. // Journal of Organic Chemistry. 2018. Vol. 83. No. 8. pp. 4840-4850.
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TY - JOUR
DO - 10.1021/acs.joc.8b00336
UR - https://doi.org/10.1021%2Facs.joc.8b00336
TI - Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes.
T2 - Journal of Organic Chemistry
AU - Aysin, Rinat
AU - Novikov, Roman G.
AU - Zubkov, Fedor I.
AU - Borisova, Kseniya K
AU - Kvyatkovskaya, Elisaveta A.
AU - Nikitina, Eugeniya V.
PY - 2018
DA - 2018/04/04 00:00:00
PB - American Chemical Society (ACS)
SP - 4840-4850
IS - 8
VL - 83
SN - 0022-3263
SN - 1520-6904
ER -
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@article{2018_Borisova,
author = {Rinat Aysin and Roman G. Novikov and Fedor I. Zubkov and Kseniya K Borisova and Elisaveta A. Kvyatkovskaya and Eugeniya V. Nikitina},
title = {Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes.},
journal = {Journal of Organic Chemistry},
year = {2018},
volume = {83},
publisher = {American Chemical Society (ACS)},
month = {apr},
url = {https://doi.org/10.1021%2Facs.joc.8b00336},
number = {8},
pages = {4840--4850},
doi = {10.1021/acs.joc.8b00336}
}
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Borisova, Kseniya K., et al. “Classical Example of Total Kinetic and Thermodynamic Control: The Diels-Alder Reaction between DMAD and Bis-furyl Dienes..” Journal of Organic Chemistry, vol. 83, no. 8, Apr. 2018, pp. 4840-4850. https://doi.org/10.1021%2Facs.joc.8b00336.
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