Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
Vasily M Muzalevskiy
1
,
Yury A Ustynyuk
1
,
Igor P. Gloriozov
1
,
Vyacheslav A. Chertkov
1
,
Alexander Yu. Rulev
2
,
Evgeniy V Kondrashov
2
,
Igor Ushakov
2
,
Alexey R Romanov
2
,
Тип публикации: Journal Article
Дата публикации: 2015-10-06
scimago Q1
wos Q2
БС1
SJR: 0.981
CiteScore: 6.7
Impact factor: 3.7
ISSN: 09476539, 15213765
PubMed ID:
26440451
General Chemistry
Catalysis
Organic Chemistry
Краткое описание
The reactions of trifluoromethylated 2-bromoenones and N,N'-dialkyl-1,2-diamines have been studied. Depending on the structures of the starting compounds, the formation of 2-trifluoroacetylpiperazine or 3-trifluoromethylpiperazine-2-ones was observed. The mechanism of the reaction is discussed in terms of multistep processes involving sequential substitution of bromine in the starting α-bromoenones and intramolecular cyclization of the captodative aminoenones as key intermediates to form the target heterocycles. The results of theoretical calculations are in perfect agreement with the experimental data. The unique role of the trifluoromethyl group in this reaction is demonstrated.
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Muzalevskiy V. M. et al. Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines // Chemistry - A European Journal. 2015. Vol. 21. No. 47. pp. 16982-16989.
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Muzalevskiy V. M., Ustynyuk Y. A., Gloriozov I. P., Chertkov V. A., Rulev A. Y., Kondrashov E. V., Ushakov I., Romanov A. R., Nenajdenko V. G. Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines // Chemistry - A European Journal. 2015. Vol. 21. No. 47. pp. 16982-16989.
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TY - JOUR
DO - 10.1002/chem.201502706
UR - https://doi.org/10.1002/chem.201502706
TI - Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines
T2 - Chemistry - A European Journal
AU - Muzalevskiy, Vasily M
AU - Ustynyuk, Yury A
AU - Gloriozov, Igor P.
AU - Chertkov, Vyacheslav A.
AU - Rulev, Alexander Yu.
AU - Kondrashov, Evgeniy V
AU - Ushakov, Igor
AU - Romanov, Alexey R
AU - Nenajdenko, Valentine G.
PY - 2015
DA - 2015/10/06
PB - Wiley
SP - 16982-16989
IS - 47
VL - 21
PMID - 26440451
SN - 0947-6539
SN - 1521-3765
ER -
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BibTex (до 50 авторов)
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@article{2015_Muzalevskiy,
author = {Vasily M Muzalevskiy and Yury A Ustynyuk and Igor P. Gloriozov and Vyacheslav A. Chertkov and Alexander Yu. Rulev and Evgeniy V Kondrashov and Igor Ushakov and Alexey R Romanov and Valentine G. Nenajdenko},
title = {Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines},
journal = {Chemistry - A European Journal},
year = {2015},
volume = {21},
publisher = {Wiley},
month = {oct},
url = {https://doi.org/10.1002/chem.201502706},
number = {47},
pages = {16982--16989},
doi = {10.1002/chem.201502706}
}
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MLA
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Muzalevskiy, Vasily M., et al. “Experimental and Theoretical Study of an Intramolecular CF3-Group Shift in the Reactions of α-Bromoenones with 1,2-Diamines.” Chemistry - A European Journal, vol. 21, no. 47, Oct. 2015, pp. 16982-16989. https://doi.org/10.1002/chem.201502706.