Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents

Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents Full article

Journal

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

Output data

Year: 2007, Volume: 43, Number: 10, Pages: 1451-1459 Pages count : 9 DOI: 10.1134/S1070428007100077

Authors

Borodkin G.I. , Zaikin P.A. , Shakirov M.M. , Shubin V.G.

Affiliations

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

Kinetic isotope effects H/D in electrophilic fluorination of aromatic compounds with NF-reagents were investigated. The small values of k(H)/k(D) (0.86-1.00) are in agreement with the polar reaction mechanism where the Wheland complex decomposition is not the limiting stage. The fluorination of 1,3,5-trideuterobenzene was established by H-1 and F-19 NMR spectroscopy to occur with a 1,2-migration of a hydrogen (deuterium) atom. The analysis of Brown-Stock relationship demonstrated that the activity of NF-reagents exceeded that of many known electrophilic systems including halogenation, but it was essentially less than the activity of elemental fluorine.

Borodkin G.I. , Zaikin P.A. , Shakirov M.M. , Shubin V.G.
Mechanism of electrophilic fluorination of aromatic compounds with NF-reagents
Russian Journal of Organic Chemistry. 2007. V.43. N10. P.1451-1459. DOI: 10.1134/S1070428007100077 WOS Scopus РИНЦ

Бородкин Г.И. , Заикин П.А. , Шакиров М.М. , Шубин В.Г.
О механизме электрофильного фторирования ароматических соединений nf-реагентами
Журнал органической химии (RUSS J ORG CHEM+). 2007. Т.43. №10. С.1460-1468. РИНЦ

Published print:

Oct 1, 2007

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