Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide

Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2005, Volume: 126, Number: 11-12, Pages: 1502-1509 Pages count : DOI: 10.1016/j.jfluchem.2005.08.010

Tags

difluoroquinolines; methoxydefluorination; liquid ammonia; regioselectivity; enthalpic control

Authors

Politanskaya LV , Malysheva LA , Beregovaya IV , Bagryanskaya IY , Gatilov YV , Malykhin EV , Shteingarts VD

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Div, NN Vorozhtsov Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

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 Me,SO. The regioselectivity of methoxydefluorination of I 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 sigma-complexes formed by the substrates with the hydroxide anion as a model nucleophile. (c) 2005 Elsevier B.V. All rights reserved.

Politanskaya L. , Malysheva L. , Beregovaya I. , Bagryanskaya I. , Gatilov Y. , Malykhin E. , Shteingarts V.
Regioselectivity and relative substrate activity of difluoroquinolines containing fluorine atoms in benzene ring in reaction with sodium methoxide
Journal of Fluorine Chemistry. 2005. V.126. N11-12. P.1502-1509. DOI: 10.1016/j.jfluchem.2005.08.010 WOS Scopus РИНЦ

Published print:

Dec 1, 2005

Web of science	WOS:000233787400010
Scopus	2-s2.0-27844600578
Elibrary	13499598
OpenAlex	W2953273404