Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Super Acids

S. Wang; Ван С.; Ya. V. Zonov; Зонов Я. В.; V. M. Karpov; Карпов В. М.; T. V. Mezhenkova; Меженкова Т. В.

doi:10.31857/S0514749224010031

Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Super Acids

Authors: Wang S.¹^,2, Zonov Y.V.¹^,2, Karpov V.M.¹, Mezhenkova T.V.¹
Affiliations:
1. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences
2. Novosibirsk State University
Issue: Vol 60, No 1 (2024)
Pages: 47-59
Section: Articles
URL: https://aspvestnik.ru/0514-7492/article/view/672218
DOI: https://doi.org/10.31857/S0514749224010031
EDN: https://elibrary.ru/ENSBKJ
ID: 672218

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Abstract

Acid-catalyzed carbonylation of a number of polyfluorinated benzocyclobuten-1-ols, as well as cyclic sulfoesters of benzocyclobuten-1,2-diols, in reaction with carbon monoxide has been carried out. The efficiency of using TfOH and FSO₃H-SbF₅ as acidic systems was evaluated. Both products of CO addition with the remaining four-membered ring — the corresponding carboxylic acids, and various products of carbonylation accompanied by its transformations (ring opening, opening followed by heterocyclization with the formation of isochromane derivatives, expansion to a five-membered one) were obtained. In some cases, the formation of polycyclic dimeric products was also observed.

Keywords

carbonylation, alcohols, carboxylic acids, polyfluorinated benzocyclobutenes, fluorosulfonic acid, trifluoromethanesulfonic acid, antimony pentafluoride

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