Abstract: A 4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl lithium derivative was found to react with 5,6,7,8-tetrafluoro- or 5,7,8-trifluoro-6-(trifluoromethyl)quinoline-N-oxides with the formation of products of aromatic nucleophilic substitution of the H atom at position 2 of the quinoline ring. The reaction regioselectivity is supported by the data of quantum-chemical calculations. Molecular and crystal structures of the obtained nitronyl nitroxides were solved by monocrystal X-ray diffraction analysis, and the nature of the radical was ascertained by electron spin resonance spectroscopy. Heterospin complexes of Cu(hfac)2 with the synthesized quinoline-substituted nitronyl nitroxides were prepared. According to X-ray diffraction analysis, seven-membered metallocycles are formed in the complexes owing to simultaneous coordination of the nitroxyl and N-oxide groups by the Cu atom. © 2020 Elsevier B.V.

Cite: Gurskaya L. , Rybalova T. , Beregovaya I. , Zaytseva E. , Kazantsev M. , Tretyakov E.
Aromatic nucleophilic substitution: A case study of the interaction of a lithiated nitronyl nitroxide with polyfluorinated quinoline-N-oxides
Journal of Fluorine Chemistry. 2020. V.237. 109613 . DOI: 10.1016/j.jfluchem.2020.109613 WOS Scopus РИНЦ OpenAlex

Dates:

Published print:

Sep 1, 2020

Identifiers:

Web of science:	WOS:000560728900007
Scopus:	2-s2.0-85088877011
Elibrary:	45394113
OpenAlex:	W3042263174

Citing:

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Scopus	5
Web of science	4
Elibrary	6
OpenAlex	6

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