Abstract: The reaction of 2-X-trifluoro-1,4-benzoquinones (X = F, Cl, Me, OMe) with triphenylphosphane in various solvents (C6H6, Et2O, THF, dioxane, MeOH, aq. dioxane and Me2SO) has been investigated. It was shown that: (1) the quinones react with PPh3 at an oxygen atom and at a carbon atom with formation of products of reduction and of triphenylphosphanodefluorination, accordingly; (2) the use of more polar solvents, such as MeOH, aq. dioxane and Me2SO, leads to an increase in products of phosphanodefluorination; (3) triphenylphosphanodefluorination of 2-X-trifluoro-1,4-benzoquinones (X = Cl, Me, OMe) takes place at positions 5 and 6 to X in ratios depending on the nature of the substituent X. Possible reasons for obtained results are discussed in detail. The entry of solvent molecule into products of phosphanodefluorination of fluoranil was observed in MeOH. The triphenyl(3,4,6,6-tetrafluoro-2-oxido-5-oxocyclohexa-1,3-dien-1-yl)phosphanium and its analogs serves as starting material for a new type of nitrogen-containing phosphorus compounds. The structures of isolated betaines were proved by the XRD and the F-19, P-31{H-1} and C-13{H-1} NMR data. (C) 2015 Elsevier B.V. All rights reserved.

Cite: Zhivetyeva S.I. , Selivanova G.A. , Goryunov L.I. , Bagryanskaya I.Y. , Shteingarts V.D.
Triphenylphosphanodefluorination of fluoranil and its derivatives
Journal of Fluorine Chemistry. 2015. V.180. P.21-32. DOI: 10.1016/j.jfluchem.2015.08.018 WOS Scopus РИНЦ

Dates:

Published print:

Dec 1, 2015

Identifiers:

Web of science	WOS:000366768800004
Scopus	2-s2.0-84941367394
Elibrary	24948935
OpenAlex	W1250038242

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