Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide
Тип публикации: Journal Article
Дата публикации: 2005-12-01
SCImago Q3
WOS Q3
БС2
SJR: 0.349
CiteScore: 3.1
Impact factor: 1.6
ISSN: 00221139, 18733328
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Краткое описание
Methoxydefluorination of 5,7-, 6,7-, 6,8-, and 5,8-difluoroquinoline (1–4) by the action of sodium methoxide has been studied in liquid ammonia and Me2SO. The regioselectivity of methoxydefluorination of 1 and 2 in the temperature interval 218–240 K in liquid ammonia and 1 and 4 in the interval 298–378 K in Me2SO as well as the activity correlation of individual reaction centers in different substrates have been established as enthalpically controlled. The overall pattern of relative reactivity is consistent with the ab initio (RHF/6-31G*) calculated relative stabilities and electronic structures of the σ-complexes formed by the substrates with the hydroxide anion as a model nucleophile.
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Politanskaya L. et al. Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide // Journal of Fluorine Chemistry. 2005. Vol. 126. No. 11-12. pp. 1502-1509.
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Politanskaya L., Malysheva L. A., Beregovaya I., Bagryanskaya I. Y., Gatilov Y. V., Malykhin E. V., Shteingarts V. D. Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide // Journal of Fluorine Chemistry. 2005. Vol. 126. No. 11-12. pp. 1502-1509.
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TY - JOUR
DO - 10.1016/j.jfluchem.2005.08.010
UR - https://doi.org/10.1016/j.jfluchem.2005.08.010
TI - Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide
T2 - Journal of Fluorine Chemistry
AU - Politanskaya, Larisa
AU - Malysheva, Lyudmila A
AU - Beregovaya, I.V.
AU - Bagryanskaya, Irina Yu.
AU - Gatilov, Yuri V.
AU - Malykhin, Evgenij V
AU - Shteingarts, Vitalij D
PY - 2005
DA - 2005/12/01
PB - Elsevier
SP - 1502-1509
IS - 11-12
VL - 126
SN - 0022-1139
SN - 1873-3328
ER -
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@article{2005_Politanskaya,
author = {Larisa Politanskaya and Lyudmila A Malysheva and I.V. Beregovaya and Irina Yu. Bagryanskaya and Yuri V. Gatilov and Evgenij V Malykhin and Vitalij D Shteingarts},
title = {Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide},
journal = {Journal of Fluorine Chemistry},
year = {2005},
volume = {126},
publisher = {Elsevier},
month = {dec},
url = {https://doi.org/10.1016/j.jfluchem.2005.08.010},
number = {11-12},
pages = {1502--1509},
doi = {10.1016/j.jfluchem.2005.08.010}
}
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MLA
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Politanskaya, Larisa, et al. “Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide.” Journal of Fluorine Chemistry, vol. 126, no. 11-12, Dec. 2005, pp. 1502-1509. https://doi.org/10.1016/j.jfluchem.2005.08.010.
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