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

Yaroslav V. Zonov, Siqi Wang, Victor M. Karpov, Tatyana V. Mezhenkova

Результат исследования: Научные публикации в периодических изданияхстатьярецензирование

Аннотация

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.

Язык оригиналаанглийский
Номер статьи109851
ЖурналJournal of Fluorine Chemistry
Том249
DOI
СостояниеОпубликовано - сен 2021

Предметные области OECD FOS+WOS

  • 1.05 НАУКИ О ЗЕМЛЕ И СМЕЖНЫЕ ЭКОЛОГИЧЕСКИЕ НАУКИ
  • 1.06 БИОЛОГИЧЕСКИЕ НАУКИ
  • 1.04 ХИМИЧЕСКИЕ НАУКИ

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Подробные сведения о темах исследования «The aliphatic ring-opening and S<sub>N</sub>Ar substitution in the reactions of perfluorobenzocycloalkenones with K<sub>2</sub>CO<sub>3</sub> in water and methanol». Вместе они формируют уникальный семантический отпечаток (fingerprint).

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