Reactions of Hexafluorobenzene

Pummer, Walter J.; Wall, Leo A.

doi:10.1126/science.127.3299.643

Cited by 26 publications

(19 citation statements)

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“…Perfluorobenzene and sodium methoxide give pentafluoroanisole. In bromo-and iodopentafluorobenzene, fluorine atoms para to bromine or iodine are replaced preferentially [418][419][420][421]. (250) Br Br In fluorinated aromatic nitrogen-containing heterocycles, fluorine is replaced preferentially in ortho and/or para positions to the nitrogen since these positions are activated for nucleophilic attacks [422].…”

Section: Arylations At Oxygenmentioning

confidence: 99%

Organic Fluorine Chemistry

Hudlický

1971

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Section: Arylations At Oxygenmentioning

confidence: 99%

Organic Fluorine Chemistry

Hudlický

1971

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“…In our earlier work [18], pentafluorophenol was prepared by refluxing hexafluorobenzene with potassium hydroxide in pyridine, which was found to be an effective solvent for this reaction. In similar reactions with hexachlorobenzene, it has been suggested [14] that pyridine has a specific, catalytic effect.…”

Section: Reactions Of Hexafluorobenzenementioning

confidence: 99%

“…With sodium methoxide in methanol, pentafluoroanisole was produced [4, 20], together with some of the tetrafluoro- p -dimethoxybenzene. With pyridine—methanol as the solvent [18], rapid reaction occurred to produce high yields (70%) of pentafluoroanisole. The tetrafluoro- p -dimethoxy benzene has also been produced by other methods [21, 22], e.g., from the reaction of diazomethane with 2,3,5,6-tetrafluorohydroquinone.…”

Section: Reactions Of Hexafluorobenzenementioning

confidence: 99%

“…Ammonium 2,3,4,5,6-pentafluorophenoxide was the only product obtained from treatment of (a) pentafluorophenol, (b) sodium pentafluorophenoxide, or (c) ammonium pentafluorophenoxide with sodamide in liquid ammonia. Thus, the tetrafluorodihydroxybenzene [18] produced in the reaction with ethanolic potassium hydroxide in pyridine probably arises form the attack of a nucleophilic species on the phenetole. In another study [19], only the phenetole was produced in 48 percent yield, and 45 percent of the hexafluorobenzene was recovered after reaction with ethanolic potassium hydroxide for 30 min at 120 °C.…”

Section: Reactions Of Hexafluorobenzenementioning

confidence: 99%

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Reactions of polyfluorobenzenes with nucleophilic reagents

Wall¹,

Pummer²,

Fearn³

et al. 1963

J. RES. NATL. BUR. STAN. SECT. A.

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Nucleophilic reactions of hexafluorob enzene and related polyfiuorobenzenes were studied in detail. R eaction of hex a fluorobenzc nc with hydroxides, alco holates, aqueous amines, and organolithium co mpounds led to the substitution of one 01' more fluorine atoms. The stru ctures of the products were determined, using near infra red a nd nuclear m agnetic resonance spectra. Fluorine is replaced more readily than chlorin e, bromine, iodine, or other groups. I n the ma jo rity of the products in which two of the fluorin es in hexafluorobenzene we re replaced, t he substituting groups were p a ra to eac h other. However, depe nding on the reagents other orientation effects were noted . The reaction mechanis ms we re a fun ction of reagents a nd co nditions. The mo t prcvalent mecha ni sm is presuma bly the di splace me nt of a fluoride anion by another anion, probably via the fo rmation of transition co mplexes of difl'erent lifetimes. Howeve r, simple ionization 0 1' attack by neutral species may occ ur under some co nditions. The diazotization a nd oxidation of pentafluoroan il ine were also inv estigated.

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“…Preparation by Direct Method. Potassium pentafluorophenoxide hydrate made from pentafluorophenol (13,14,15) can be used directly to prepare 1,1,2,2tetrafluoroethyl 2,3,4,5,6-~entafluorophenyl ether (IX) by reacting it with tetrafluoroethylene in dimethylformamide at 80°C. The hydrated lithium pentafluorophenoxide behaves in a similar fashion except that the yields are somewhat lower.…”

Section: 3456-pentaf Luorophenyl 122-trifluorovinyl Ether (Xi)mentioning

confidence: 99%

1,2,2‐Trifluorovinyl phenyl ether and 2,3,4,5,6‐pentafluorophenyl 1,2,2‐trifluorovinyl ether and their polymers

Pummer

Wall

1963

Polymer Engineering & Sci

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1,2,2,‐Trifluorovinyl phenyl ether and 2,3,4,5,6,‐pentafluorophenyl 1,2,2‐trifluorovinyl ethers have been prepared, and the nucleophilic reactions of the phenoxide and 2,3,4,5‐pentafluorophenoxide salts with tetrafluoroethylene have been investigated. In general, it is some‐what difficult to control the reaction so as to produce the desired olefinic monomer. Under truly anhydrous conditions and when other sources of active protons are avoided, the olefin is the chief product if excess tetrafluoroethylene is used. The monomer produced is very reactive with phenoxide ions, and the diphenoxyolefins are the chief secondary products. Both monomers failed to polymerize under normal, free radical conditions. With boron trifluoride an oily material was obtained from the trifluorovinyl phenyl ether. High pressure and gamma rays converted both monomers into polymers.

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Reactions of Hexafluorobenzene

Cited by 26 publications

References 4 publications

Organic Fluorine Chemistry

Organic Fluorine Chemistry

Reactions of polyfluorobenzenes with nucleophilic reagents

1,2,2‐Trifluorovinyl phenyl ether and 2,3,4,5,6‐pentafluorophenyl 1,2,2‐trifluorovinyl ether and their polymers

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