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Title: Compounds of transition metals with sigma-bonded fluorine-containing groups. VI. A new method for the perfluoroalkylation of aromatic compounds by means of the perfluoroalkyl complexes of iron

Abstract

The action of silver fluoride on C/sub 3/F/sub 7/Fe(CO)/sub 4/)I in the presence of aromatic substrates (benzene, toluene, anisole, furan) at 20/sup 0/C led to the formation of perfluoroalkylation products. On the basis of the isomeric composition of the obtained perfluoropropyl derivatives of toluene and anisole it was concluded that the process was cationic in nature. Perfluoropropyltoluenes were obtained when C/sub 3/F/sub 7/Fe(CO)/sub 4/OCOCF/sub 3/ or (C/sub 3/F/sub 7/)/sub 2/Fe(CO)/sub 4/ were heated in toluene. The cationic complex (C/sub 3/F/sub 7/Fe(CO)/sub 4/)/sup +/BF/sub 4//sup -/ reacts with dimethylaniline and with sodium p-toluene-thiolate to form p-perfluoropropyldimethylaniline and p-tolyl perfluoropropyl sulfide.

Authors:
; ;
Publication Date:
Research Org.:
Institute of Organic Chemistry, Kiev, USSR
OSTI Identifier:
6224893
Resource Type:
Journal Article
Journal Name:
J. Org. Chem. USSR (Engl. Transl.); (United States)
Additional Journal Information:
Journal Volume: 21:9; Other Information: Translated from Zh. Org. Khim.; 21: No.9, 1852-1857(Sep 1985)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; AROMATICS; ALKYLATION; FLUORINATION; CARBONYLS; ACTIVATION ENERGY; IRON COMPLEXES; IRON IODIDES; ORGANIC FLUORINE COMPOUNDS; SILVER FLUORIDES; CATALYTIC EFFECTS; ANISOLE; BENZENE; CATIONS; CHEMICAL BONDS; CHEMICAL SHIFT; CHLOROFORM; COMPLEXOMETRY; DEUTERIUM COMPOUNDS; FLUORINE 19; FURANS; ISOMERIZATION; NMR SPECTRA; TOLUENE; ALKYLATED AROMATICS; CHARGED PARTICLES; CHEMICAL REACTIONS; CHLORINATED ALIPHATIC HYDROCARBONS; COMPLEXES; ENERGY; ETHERS; FLUORIDES; FLUORINE COMPOUNDS; FLUORINE ISOTOPES; HALIDES; HALOGEN COMPOUNDS; HALOGENATED ALIPHATIC HYDROCARBONS; HALOGENATION; HETEROCYCLIC COMPOUNDS; HYDROCARBONS; HYDROGEN COMPOUNDS; IODIDES; IODINE COMPOUNDS; IONS; IRON COMPOUNDS; ISOTOPES; LIGHT NUCLEI; NUCLEI; ODD-EVEN NUCLEI; ORGANIC CHLORINE COMPOUNDS; ORGANIC COMPOUNDS; ORGANIC HALOGEN COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; SILVER COMPOUNDS; SPECTRA; STABLE ISOTOPES; TRANSITION ELEMENT COMPLEXES; TRANSITION ELEMENT COMPOUNDS; 400201* - Chemical & Physicochemical Properties

Citation Formats

Gerus, I I, Yagupol'skii, Yu L, and Yagupol'skii, L M. Compounds of transition metals with sigma-bonded fluorine-containing groups. VI. A new method for the perfluoroalkylation of aromatic compounds by means of the perfluoroalkyl complexes of iron. United States: N. p., 1986. Web.
Gerus, I I, Yagupol'skii, Yu L, & Yagupol'skii, L M. Compounds of transition metals with sigma-bonded fluorine-containing groups. VI. A new method for the perfluoroalkylation of aromatic compounds by means of the perfluoroalkyl complexes of iron. United States.
Gerus, I I, Yagupol'skii, Yu L, and Yagupol'skii, L M. 1986. "Compounds of transition metals with sigma-bonded fluorine-containing groups. VI. A new method for the perfluoroalkylation of aromatic compounds by means of the perfluoroalkyl complexes of iron". United States.
@article{osti_6224893,
title = {Compounds of transition metals with sigma-bonded fluorine-containing groups. VI. A new method for the perfluoroalkylation of aromatic compounds by means of the perfluoroalkyl complexes of iron},
author = {Gerus, I I and Yagupol'skii, Yu L and Yagupol'skii, L M},
abstractNote = {The action of silver fluoride on C/sub 3/F/sub 7/Fe(CO)/sub 4/)I in the presence of aromatic substrates (benzene, toluene, anisole, furan) at 20/sup 0/C led to the formation of perfluoroalkylation products. On the basis of the isomeric composition of the obtained perfluoropropyl derivatives of toluene and anisole it was concluded that the process was cationic in nature. Perfluoropropyltoluenes were obtained when C/sub 3/F/sub 7/Fe(CO)/sub 4/OCOCF/sub 3/ or (C/sub 3/F/sub 7/)/sub 2/Fe(CO)/sub 4/ were heated in toluene. The cationic complex (C/sub 3/F/sub 7/Fe(CO)/sub 4/)/sup +/BF/sub 4//sup -/ reacts with dimethylaniline and with sodium p-toluene-thiolate to form p-perfluoropropyldimethylaniline and p-tolyl perfluoropropyl sulfide.},
doi = {},
url = {https://www.osti.gov/biblio/6224893}, journal = {J. Org. Chem. USSR (Engl. Transl.); (United States)},
number = ,
volume = 21:9,
place = {United States},
year = {Mon Feb 10 00:00:00 EST 1986},
month = {Mon Feb 10 00:00:00 EST 1986}
}