hexafluoropropan-2-o1 (HFP) appears as a solvent with properties at the extreme. Its combination of low nucleophilicity, high hydrogen bonding donor strength, low hydrogen bonding acceptor strength, high polarity and high ionizing power makes it an ideal solvent for radical cations. Applications of HFP as a solvent for EPR spectroscopy and mechanistic studies of radical cations as intermediates in electrophilic aromatic substitution, photochemistry and spin trapping are described.
trometer using tetrame^hylsilane as an internal standard. Vapor phase chromatography was performed on a Perkin-Elmer Model 226 capillary gas chromatograph equipped with 300 ft X 0.01 in. DC-550 silicone columns.Hydrogenation of Phenylmercury Acetate. In a typical experiment a Parr low-pressure reactor16 was charged with 6 g (17.8 mmol) of phenylmercury acetate, 90 mg (0.1 mmol) of tris(triphenylphosphine)rhodium(I) chloride, and 100 ml of methanol. The clear, yellow solution was pressurized with hydrogen to 36 psig at room temperature, and the reaction mixture was shaken overnight. The reactor pressure declined to ~19 psig, corresponding to the consumption of ~20 mmol of hydrogen. From the reaction was recovered 2.9 g of mercury (82%). The methanol was poured into water and was extracted with pentane. The extract was dried over magnesium sulfate and analyzed for benzene by VPC using p-xylene as an internal standard. The benzene yield was 1.2 g (85%).Under similar conditions the following catalysts gave the benzene yields shown: tris(triphenylphosphine)ruthenium(II) chloride, 13%; hydridotris(triphenylphosphine)ruthenium(II) chloride, 17%; tetrakis(triphenylphosphine)palladium(0), 24%; tetrakis(triphenylphosphine)platinum(O), 16%; bis(triphenylphosphine)platinum(II) chloride, 14%. Preparation of Bimetallic Complex (I). A solution of 264 mg (0.78 mmol) of phenylmercury acetate in 5 ml of chloroform was added to a solution of 691 mg (0.75 mmol) of tris(triphenylphosphine)rhodium(I) chloride in 5 ml of chloroform. The solution was stirred at room temperature for 15 min and the chloroform was removed by evaporation. The residue was recrystallized from 25 ml of methanol to yield 474 mg (63%) of yellow crystals, mp 184-186°.
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