Abstract: In the reactions with aqueous K2CO3, perfluorinated benzocyclobuten-1-one, 3-R-indan-1-ones and 4-R-tetralin-1-ones (R = F, C2F5) undergo selective cleavage of the СO–С(Ar) bond to yield (2,3,4,5-tetrafluorophenyl)perfluoroalkanoic acids after acidification of the reaction mixture; benzocyclobuten-1-ones and indan-1-ones bearing perfluoroalkyl or perfluorophenyl group at C(2) react predominantly or exclusively with cleavage of the СO–С(2) bond to form 2-substituted tetrafluorobenzoic acids; 3,3-diethylindan-1-one gives 5- and 7-hydroxy derivatives as the only products, whereas for 3-ethylindan-1-one SNAr substitution of fluorine atoms and the five-membered ring-opening are competitive processes; benzocyclobutene-1,2-dione, indan-1,3-dione and tetralin-1,4-dione undergo cleavage of the СO–С(Ar) bond to yield ω-(2,3,4,5-tetrafluorophenyl)-ω-oxoperfluoroalkanoic acids, but only the former reacts selectively, in the other diketones, the СO–С(2) bond cleavage or/and nucleophilic substitution of fluorine atoms also occurs. Perfluobenzocyclobuten-1-one and -1,2-dione react with K2CO3 in methanol similar to their transformation in the aqueous medium to form methyl (2,3,4,5-tetrafluorophenyl)difluоroacetate and - oxoacetate, respectively, whereas perfluoroindan-1-one with K2CO3 in methanol gives 5-methoxyperfluоroindan-1-one. © 2021 Elsevier B.V.

Cite: Zonov Y.V. , Wang S. , Karpov V.M. , Mezhenkova T.V.
The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol
Journal of Fluorine Chemistry. 2021. V.249. 109851 . DOI: 10.1016/j.jfluchem.2021.109851 WOS Scopus РИНЦ

Identifiers:

Web of science	WOS:000685602900008
Scopus	2-s2.0-85111027898
Elibrary	46934007
OpenAlex	W3185556578

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