Bis pentafluoroethyl

Silver(I) fluoride is most useful for the conversion of 2-chloro-4,6-bis(pentafluoroethyl)-1,3,5-triazine, 2-chloro-4,6-bis(heptafluoropropyl)-l,3,5-triazine, and 2,4,6-trichloro-l,3,5-triazine to the corresponding fluoro-l,3,5-triazines. 2-Fluoro-4,6-bis(pentafluoroethyl)-l,3,5-triazineis obtained in 98 % yield, and 2-fluoro-4,6-bis(heptafluoropropyl)-l,3,5-triazinein 95 % yield, (both at 90 C for 30 minutes), while 2,4,6-trifluoro-l,3,5-triazine is available in 78.5% yield (at 100CC for 1 hour). Silver(II) fluoride, mercury(II) fluoride and antimony dichloride trifluoride give lower yields of these compounds.34... 

Similar results are found in the older literature. Trifluoroacetonitrile over cobalt(III) fluoride gives102 some A.AAdifluoropentafluoroethylamine, and over silver(II) fluoride, the azo compound bis(pentafluoroethyl)diazene is the major product.103 Perfluorobutanonitrile behaves similarly. 

The interaction between perfluoro-2-methylpent-2-ene and ethylenedia-mine in the presence of triethylamine forms 5,9-bis(pentafluoroethyl)-6,8,8-tris(trifhioromethyl)-9-fluoro-1,4-diazabicyclo[5.2.0]nona-4,6-diene 148. With hexane-1,6-diamine, the product is 1 l-(pentafluoroethyl)-10-trifhioro-methyl-1,8-diazabicyclo[7.2.0]undeca-8,10-diene 149 (99IZY1578). The structure of 148 was confirmed by X-ray analysis (Fig. 7) (99IZV1578). 

Fig. 7. Crystal structure of 9-fluoro-5,9-bis(pentafluoroethyl)-6,8,8-tris(trifluoromethyl)-l,4-diazabicyclo[5.2.0]nona-4,6-diene 148 acording to X-ray diffraction data (99IZV1578).

Bis pentafluoroethyl ditellurium was isolated in low yields from reaction mixtures obtained by heating tetratellurium bis[hcxafluoroarsenate] to 100° under 15 atmospheres of tetrafluoroethene1 2. 

Bis[pentafluoroethyl] Ditcllurium2 In a 40 m/ Monel reactor, 9.4 g (10.6 mmol) or tetratellurium bis[hexafluoroarscnate] are heated at 100° for 11 days in the presence of tetrafluoroethene (15 atmospheres pressure). The yellow-red liquid (8.3 g) is separated from arsenic at low temperature by freezing out arsenic trifluoride. The ditellurium product is isolated from the decanted liquid by preparative vapor phase chromatography yield 12%. 

Bis[pentafluoroethyl] ditellurium is a reddish liquid that decomposes in light to tellurium and bis[pentafluoroethyl] tellurium. The ditellurium is stable in the dark at 18° for several months. The vapor pressure at 25° is 4.6 torr. This method has not yet been used for the preparation of other perfluoroalkyl ditellurium derivatives. 

Diphenyl ditellurium and xenon difluoride produced phenyl tellurium pentafluoride1. Bis[pentafluorophenyl] ditellurium and xenon difluoride or fluorine diluted with nitrogen at low temperatures yielded pentafluorophenyl tellurium trifluoride2. Similar reactions were carried out with bis[pentafluoroethyl] ditellurium3. 

Bis[pentafluoroethyl] ditellurium reacted with a slurry of xenon difluoride/sulfuryl fluoride in the temperature range — 45 to 20°. Pentafluoroethyl tellurium trifluoride was obtained as a crystalline solid in quantitative yield5. 

The selective alkylation of tellurium tetrachloride10 and tetrabromide11 to a diorgano tellurium compound was achieved with bis[trifluoromethyl] mercury10 11 and the bipyridyl adduct of bis[pentafluoroethyl] mercury11. 

Bis[pentafluoroethyl] tellurium treated with excess fluoride at — 78° produces trans-bisjpentafluoroethyl] tellurium tetrafluoride as one of the products2. Bisfpentafluorophe-nyl] tellurium reacted in fluorotrichloromethane at — 35° with fluorine diluted by nitrogen to yield bis[pentafluorophenyl] tellurium tetrafluoride. Excess fluorine attacks the aromatic ring ultimately producing bis[perfluorocyclohexyl] tellurium tetrafluoride3. 

Bis pentafluoroethyl] tellurium difluoride (m.p. 57°) was obtained in quantitative yield from bis[pentafluoroethyl] tellurium and a mixture of xenon difluoride and sulfuryl chloride fluoride at — 45°4. 

Cesium bis pentafluoroethyl]trifluorotellurate(IV) was prepared similarly3. The bis[tri-fluoromethyl]trichlorotellurates were similarly obtained from bis[trifluoromethyl]tellurium dichloride and the metal chlorides in acetonitrile at — 5°. The correspondings bi trifluoro-methyl]tribromotellurates(TV) were detected in solution by 19F-NMR spectroscopy but could not be isolated2. 

When treated with excess chlorine fluoride at 20° bis[pentafluoroethyl] tellurium difluoride formed trans-bis pentafluoroethyl tellurium tetrafluoride2 3. 

The reaction of fluoro- or chlorofluoroalkenes with the sulfur tetrafluoride/hydrogen fluoride/ sulfur monochloride system leads to perfluoroalkanesulfenyl chlorides, (sulfanyl)sulfenyl chlorides, sulfides and polysulfides.511 514 Tetrafluoroethene reacts with sulfur tetrafluoride/hydrogen fluoride in the presence of 1 equivalent of sulfur monochloride at 80°C to yield a mixture of pentafluoroethanesulfenyl chloride (4), (pentafluoroethanesulfanyl)sulfenyl chloride (5) and bis(pentafluoroethyl) trisulfide (6).513 Other examples of this type of reaction are summarized in Table 37. 

When stored at — 18°, the compound decomposed slightly to give the bis[pentafluoroethyl] ditellurium and diselenium compounds. ... 

When shaken with mercury, solutions of ditellurium compounds in benzene or neat bis[pentafluoroethyl] ditellurium form bis[organotelluro] mercury products. 

Fluorination with elemental fluorine diluted 1 20 with nitrogen was used to prepare pentqfluorophenyl tellurium trifluoride from bis[pentafluorophenyl] ditellurium at — 60° with fluorotrichloromethane as the reaction medium. The yield in this reaction was 80%. 4-M ethoxy phenyl tellurium trifluoride was obtained by electrochemical oxidation of the diaryl ditellurium in 0.5 M hydrofluoric acid at platinum electrodes. Bis[pentafluoroethyl] ditellurium and chlorine fluoride (1 6) reacted at — 78° to give pentafluoroethyl tellurium trifluoride, a white solid melting at 95° The same compound was obtained with xenon difluoride as the fluorinating agent and melted at 143° . ... 

Similarly, thermolysis (150°C) of 3-diazodecafluoropentane in the presence of benzene yielded 7,7-bis(pentafluoroethyl)cyclohcpta-l,3,5-triene in 22% yield, rather than the valence tautomeric norcaradiene derivative. ... 

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