Unusual lability of pentafluorophenoxy group in reactions of potassium aroxides with pentafluoropyridine

Unusual lability of pentafluorophenoxy group in reactions of potassium aroxides with pentafluoropyridine Full article

Journal

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

Output data

Year: 2002, Volume: 38, Number: 1, Pages: 115-125 Pages count : 11 DOI: 10.1023/A:1015371212613

Authors

Vlasov VM ¹ , Aksenov VV ¹ , Rodionov PP ¹ , Beregovaya IV ¹ , Shchegoleva LN ¹

Affiliations

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

The kinetics of the reactions of pentafluoropyridine with potassium aroxides, leading to formation of polyfluorinated aryl pyridyl ethers, conform to the Bronsted equation. The data obtained for potassium pentafluorophenoxide deviate from the general correlation because of readily occuring reverse reaction, replacement of the pentafluorophenoxy group by released fluoride ion. PM3 calculations of the electronic structure of the reagents, intermediate sigma-complexes, and products showed that the replacement of fluorine in pentafluoropyridine is a charge-controlled process, whereas unusually easy replacement of the pentafluorophenoxy group in the corresponding aryl pyridyl ether by fluorine is explained by structural features of its lowest unoccupied molecular orbital.

Vlasov V. , Aksenov V. , Rodionov P. , Beregovaya I. , Shchegoleva L.
Unusual lability of pentafluorophenoxy group in reactions of potassium aroxides with pentafluoropyridine
Russian Journal of Organic Chemistry. 2002. V.38. N1. P.115-125. DOI: 10.1023/A:1015371212613 WOS Scopus РИНЦ

Web of science	WOS:000174771400021
Scopus	2-s2.0-0036262052
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