Reactions of 4-substituted-1-[(difluoromethyl)sulfinyl]polyfluorobenzenes with phenolate anion

Reactions of 4-substituted-1-[(difluoromethyl)sulfinyl]polyfluorobenzenes with phenolate anion Full article

Journal

ARKIVOC
ISSN: 1551-7004 , E-ISSN: 1551-7012

Output data

Year: 2020, Pages: 344-361 Pages count : 18 DOI: 10.24820/ark.5550190.p011.262

Tags

Polyfluoroaromatic compounds; sulfoxides; sodium phenolate; aromatic nucleophilic substitution

Authors

Koshcheev Borislav V. ¹ , Bredikhin Roman A. ¹ , Maksimov Alexander M. ¹ , Platonov Vyacheslav E. ¹ , Andreev Rodion V. ¹

Affiliations

1	(Данные Web of science) Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

The reactions of 4-substituted-polyfluorinated-[(difluoromethyl)sulfinyl]benzenes ([4-X-C6F4S(O)CHF2 [X = H, CF3 and C6F5S(O)]) with phenolate anion in benzene, Et2O and CH3CN have been investigated. The reactions of the substrate (X = H, CF3) and sodium phenolate in equal amounts resulted in the formation of mixtures of the starting compound, 2-phenoxyderivative and disubstituted products. The two-fold amount of the phenolate afforded the 2,6-disubstituted products for X = H in MeCN and for X = CF3 in Et2O. At the same time, 4-CF3-C6F4S(O)CHF2 in CH3CN gave a mixture of the 2,6- and 2,5-bis(phenoxy) derivatives. Quantum chemical calculations have been performed to explain this phenomenon. For X = C 6 F 5 S(0) in MeCN, the reaction was accompanied by sulfinyl moiety ipso-substitution. [GRAPHICS] .

Koshcheev B.V. , Bredikhin R.A. , Maksimov A.M. , Platonov V.E. , Andreev R.V.
Reactions of 4-substituted-1-[(difluoromethyl)sulfinyl]polyfluorobenzenes with phenolate anion

ARKIVOC. 2020. P.344-361. DOI: 10.24820/ark.5550190.p011.262 WOS Scopus

Full text from publisher

Published online:

Sep 21, 2020

Web of science	WOS:000584517600030
Scopus	2-s2.0-85094142769
OpenAlex	W3088526293