Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols

Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols Full article

Journal

Journal of Fluorine Chemistry
ISSN: 1873-3328 , E-ISSN: 0022-1139

Output data

Year: 2025, Volume: 282, Article number : 110402, Pages count : DOI: 10.1016/j.jfluchem.2025.110402

Authors

Kudryavtseva Ekaterina N. ¹ , Lichitsky Boris V. ¹ , Tretyakov Evgeny V. ¹

Affiliations

1	N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Pr. 47, Moscow 119991, Russian Federation

Reaction of hexafluoro-1,4-naphthoquinone with various phenols was studied for the first time. It was shown that sodium acetate is a convenient reagent for implementation of the process. The investigated condensation led exclusively to substitution of two fluorine atoms in the quinone core. Based on performed research the method for preparation of substituted 2,3-diaryloxy-5,6,7,8-tetrafluoronaphthalene-1,4-diones was elaborated. Using similar conditions pentafluorobenzo[a]phenoxazine derivatives were obtained from 2-aminophenols. In contrast to phenols cyclic 1,3-diketones in the reaction with perfluoronaphthoquinone act as C-nucleophiles resulting in fluorinated polycondensed furans. Structures of key obtained products were proved using X-ray analysis.

Kudryavtseva E.N. , Lichitsky B.V. , Tretyakov E.V.
Investigation of the reaction of hexafluoro-1,4-naphthoquinone with substituted phenols
Journal of Fluorine Chemistry. 2025. V.282. 110402 . DOI: 10.1016/j.jfluchem.2025.110402 WOS Scopus OpenAlex

Submitted:	Jan 13, 2025
Published online:	Feb 12, 2025

Web of science:	WOS:001426617100001
Scopus:	2-s2.0-85217436797
OpenAlex:	W4407401637

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