Abstract: Carbonylation of polyfluorinated benzocyclobutenes with CO in an SbF5 medium readily proceeds at room temperature and atmospheric pressure and it is followed by four-membered ring transformations. Perfluorinated benzocyclobutene, 3- and 4-methyl-benzocyclobutenes add two CO molecules to form, after ring opening and following heterocyclization, isochromene derivatives. Hydrolysis of the reaction mixtures gives corresponding 4-carboxy-1H-isochromenes and 2-(carboxymethyl)benzoic acids. The carbonylation of perfluorinated 1-methyl-, 1-ethyl- and 1-isopropyl-benzocyclobutene gives salts of 2-(2-methylphenyl)alk-2-enoyl cations and the corresponding acids after hydrolysis of the latters. Perfluoro-1-phenylbenzocyclobutene in the reaction with CO-SbF5 transforms into a salt of perfluro-4-phenylisochromenyl cation, its hydrolysis gives perfluro-4-phenylisochromen-1-one. (C) 2014 Elsevier B.V. All rights reserved.

Cite: Zonov Y.V. , Karpov V.M. , Platonov V.E.
The first carbonylation of perfluoroorganic compounds: The reactions of perfluorobenzocyclobutene and its perfluoroalkyl and pentafluorophenyl derivatives with CO in SbF5 medium
Journal of Fluorine Chemistry. 2014. V.162. P.71-77. DOI: 10.1016/j.jfluchem.2014.03.008 WOS Scopus РИНЦ OpenAlex

Dates:

Published print:

Jun 1, 2014

Identifiers:

Web of science:	WOS:000336827000010
Scopus:	2-s2.0-84899566219
Elibrary:	21874236
OpenAlex:	W1970408865

Citing:

DB	Citing
Web of science	13
Scopus	11
Elibrary	14
OpenAlex	16

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