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The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol. / Zonov, Yaroslav V.; Wang, Siqi; Karpov, Victor M. et al.

In: Journal of Fluorine Chemistry, Vol. 249, 109851, 09.2021.

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Zonov YV, Wang S, Karpov VM, Mezhenkova TV. The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol. Journal of Fluorine Chemistry. 2021 Sept;249:109851. doi: 10.1016/j.jfluchem.2021.109851

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@article{670d904e3c1c4a13ace48b6f46c16fb5,
title = "The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol",
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.",
keywords = "Benzocyclobutenone, Carboxylic acid, Indanone, Ketone, Perfluorinated, Ring-opening, Tetralon",
author = "Zonov, {Yaroslav V.} and Siqi Wang and Karpov, {Victor M.} and Mezhenkova, {Tatyana V.}",
note = "Funding Information: The authors are grateful to the Multi-Access Chemical Research Center of SB RAS for spectral and analytical measurements. Siqi Wang thanks the China Scholarship Council for support and funding. Publisher Copyright: {\textcopyright} 2021 Elsevier B.V. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.",
year = "2021",
month = sep,
doi = "10.1016/j.jfluchem.2021.109851",
language = "English",
volume = "249",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - The aliphatic ring-opening and SNAr substitution in the reactions of perfluorobenzocycloalkenones with K2CO3 in water and methanol

AU - Zonov, Yaroslav V.

AU - Wang, Siqi

AU - Karpov, Victor M.

AU - Mezhenkova, Tatyana V.

N1 - Funding Information: The authors are grateful to the Multi-Access Chemical Research Center of SB RAS for spectral and analytical measurements. Siqi Wang thanks the China Scholarship Council for support and funding. Publisher Copyright: © 2021 Elsevier B.V. Copyright: Copyright 2021 Elsevier B.V., All rights reserved.

PY - 2021/9

Y1 - 2021/9

N2 - 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.

AB - 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.

KW - Benzocyclobutenone

KW - Carboxylic acid

KW - Indanone

KW - Ketone

KW - Perfluorinated

KW - Ring-opening

KW - Tetralon

UR - http://www.scopus.com/inward/record.url?scp=85111027898&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2021.109851

DO - 10.1016/j.jfluchem.2021.109851

M3 - Article

AN - SCOPUS:85111027898

VL - 249

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 109851

ER -

ID: 29131500