Abstract: 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.

Cite: 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 OpenAlex

Dates:

Published print:

Dec 1, 2005

Identifiers:

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

Citing:

DB	Citing
Web of science	10
Scopus	12
Elibrary	11
OpenAlex	13

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