Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Superacids

Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Superacids Full article

Journal

Russian Journal of Organic Chemistry
ISSN: 1070-4280 , E-ISSN: 1608-3393

Output data

Year: 2024, Volume: 60, Number: 1, Pages: 1-11 Pages count : 11 DOI: 10.1134/s1070428024010019

Tags

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

Authors

Wang S. ^1,2 , Zonov Ya.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

Acid-catalyzed carbonylation of a series of polyfluorinated benzocyclobuten-1-ols, as well as cyclic sulfuric acid esters derived from benzocyclobutene-1,2-diols, with carbon monoxide in the presence of TfOH and FSO3H–SbF5 gave both CO addition products with retention of the four-membered ring (the corresponding carboxylic acids) and carbonylation products. In the latter case, the reaction was accompanied by ring opening, ring opening with subsequent heterocyclization to isochroman derivatives, and ring expansion to five-membered cycle. Polycyclic dimeric products were also formed in some cases.

Wang S. , Zonov Y.V. , Karpov V.M. , Mezhenkova T.V.
Carbonylation and Other Transformations of Polyfluorobenzocyclobutenols in Superacids
Russian Journal of Organic Chemistry. 2024. V.60. N1. P.1-11. DOI: 10.1134/s1070428024010019

Submitted:	Jul 29, 2022
Accepted:	Aug 11, 2022
Published print:	Apr 25, 2024

OpenAlex

W4395445225