Arene complexes of transition metals in reactions with nucleophilic reagents. XVII. Nucleophilic substitution of the fluorine atom by alkoxy groups, catalyzed by the (/eta/-benzene)(/eta/-ethyltetramethylcyclopentadienyl)rhodium(III) dication, in the reaction of fluoroarenes with alcohols
Effective catalysis by the ((/eta/-C/sub 6/H/sub 6/)Rh(/eta/-C/sub 5/EtMe/sub 4/))/sup 2+/(PF/sub 6//sup /minus//)/sub 2/ complex, discovered earlier in the case of methoxydefluorination, occurs during the nucleophilic substitution of a fluorine atom by alkoxy groups in the reactions of fluoroarenes with a wide range of alcohols in the absence of alkalis. By means of fluorobenzene it was established that the accumulation rate of the ethers depends substantially on the structure of the nucleophile. For the case of the production of the compounds C/sub 10/H/sub 21/OC/sub 6/H/sub 5/ and C/sub 16/H/sub 33/-2,4,6-Me/sub 3/C/sub 6/H/sub 2/ it was shown that higher alkyl aryl ethers can be synthesized with yields of 65-70%, calculated on the fluoroarene, and up to 900% calculated on the catalyst. By the synthesis of benzodioxane in the reaction of o-fluorophenol with 2-chloroethanol it was demonstrated that heterocyclic compounds can be obtained if bifunctional substrates and reagents are used.
- Research Organization:
- Novosibirsk Institute of Organic Chemistry (USSR)
- OSTI ID:
- 5949871
- Journal Information:
- J. Org. Chem. USSR (Engl. Transl.); (United States), Journal Name: J. Org. Chem. USSR (Engl. Transl.); (United States) Vol. 24:2; ISSN JOCYA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
400201* -- Chemical & Physicochemical Properties
ALCOHOLS
ALKOXIDES
AROMATICS
CATALYSIS
CATALYSTS
CATALYTIC EFFECTS
CHEMICAL EXPLOSIVES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CHROMATOGRAPHY
COMPLEXES
DEHALOGENATION
ELEMENTS
ETHERS
EXPLOSIVES
FLUORINATED AROMATIC HYDROCARBONS
FLUORINE
HALOGENATED AROMATIC HYDROCARBONS
HALOGENS
HYDROXY COMPOUNDS
MASS SPECTRA
MOLECULAR STRUCTURE
NITRO COMPOUNDS
NITROMETHANE
NONMETALS
ORGANIC COMPOUNDS
ORGANIC FLUORINE COMPOUNDS
ORGANIC HALOGEN COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
RHODIUM COMPLEXES
SEPARATION PROCESSES
SPECTRA
SYNTHESIS
TRANSITION ELEMENT COMPLEXES
YIELDS