Diphenyl copper iodide

CuFi2N4P2C24H28, Copper(II), (2,9-dimethyI-3,10-diphenyl-l, 4,8,11 -tetraazacyclotet-radeca-l,3,8,10-tetraene)-, bis[hexa-fluorophosphate(l-)], 22 10 Cul, Copper iodide, 22 101 CuN307SC,3H,4, Copper(II), (1,10-phenan-throline)[serinato(l-)]-, sulfate, 21 115 CUN4O2C10H18, Copper(II), [1,4,8,11-tetra-zacyclotetradecane-5,7-dionato(2-)]-, 23 83... 

CuF12N4P2C24Ha, Copper(ll), (2,9-dimethyl-3,10-diphenyl-l, 4,8,11-tetraazacyclotet-radeca-l,3,8,10-tetraene)-, bis-(hexafluorophosphate(l-)], 22 10 Cul, Copper iodide, 22 101... 

The similar alkoxide- or hydroxide-induced trifluoromethylation was also found to work with other electrophiles. Diphenyl disulfide can be trifluoromethylated to give trifluoromethyl phenyl sulfide in 87% yield (eq 4). Methyl benzoate can be trifluoromethylated to generate 2,2,2-trifluoroacetophenone in 30% yield at temperatures between —50°C and —20°C. Trifluo-romethylcopper (CF3CU) can be generated in situ with trifluoromethyl sulfone, f-BuOK, and copper iodide (Cul), and it then further reacts with iodobenzene at 80 °C for 20 h to give a,a,a-trifluorotoluene in 26% 3neld. ... 

Carboxylic acids, a-bromination of 55, 31 CARBOXYLIC ACID CHLORIDES, ketones from, 55, 122 CARBYLAMINE REACTION, 55, 96 Ceric ammonium nitrate [Ammonium hexa mtrocerate(IV)[, 55, 43 Chlorine, 55, 33, 35, 63 CHROMIUM TRIOXIDE-PYRIDINE COMPLEX, preparation in situ, 55, 84 Cinnamomtnle, a-phenyl- [2-Propeneni-tnle 2,3-diphenyl-], 55, 92 Copper(l) iodide, 55, 105, 123, 124 Copper thiophenoxide [Benzenethiol, copper(I) salt], 55, 123 CYCLIZATION, free radical, 55, 57 CYCLOBUTADIENE, 55, 43 Cyclobutadieneiron tricarbonyl [Iron, tn-carbonyl(r)4-l,3-cyclo-butadiene)-], 55,43... 

Manganese(III) acetate, 171 4-Methoxy-2,2,6,6-tetramethyl-l -oxopiperidinium chloride, 183 Palladium(II) chloride-Copper(II) chloride, 235 Samarium(II) iodide, 270 Tetrachlorotris[bis(l,4-diphenyl-phosphine)butane]diruthenium, 288... 

As stated above, intermolecular coupling reactions between carbon atoms are of limited use. In the classical Wurtz reaction two identical primary alkyl iodide molecules are reduced by sodium. n-Hectane (C100H202), for example, has been made by this method in 60% yield (G. Stallberg, 1956). The unsymmetrical coupling of two alkyl halides can be achieved via dialkylcuprates. The first halide, which may have a branched carbon chain, is lithiated and allowed to react with copper(I) salts. The resulting dialkylcuprate can then be coupled with alkyl or aryl iodides or bromides. Although the reaction probably involves radicals it is quite stereoselective and leads to inversion of chiral halides. For example, lithium diphenyl-cuprate reacts with (R)-2-bromobutane with 90% stereoselectivity to form (S)-2-phenylbutane (G.M. Whitesides, 1969). 

The solvatochromic effects on UV/visible spectra of certain solutes are so large, that they can conveniently be employed as probes for certain solvating properties of the solvents. Those that have enjoyed widespread application in this capacity are discussed in Chapter 4. They include 2,6-diphenyl -4-(2,4,6-triphenyl-l-pyridino)-phenoxide, 4-methoxynitrobenzene, 4-(dimethylamino)-nitrobenzene, for the estimation of the polarity of solvents, acetylacetonato-N,N,N, N -tetramethylethylenediamino-copper(II) perchlorate, 4-nitrophenol, and 4-nitroaniline, for the estimation of the electron pair donicity of solvents, 4-carboxymethyl-l-ethylpyridinium iodide, 4-cyano-l-ethylpyridinium iodide, and bis-c/.v-1, lO-phenanthrolinodicyano-iron(II) for the estimation of the hydrogen bond donation abilities of solvents (Marcus 1993). 

Dinitro-p-diphenyl carbizide Arsenic (III), As+3 Silver nitrate Copper (II) sulfate Potassium tri-iodide (Kl + l2)... 

Nitrophenyl Phenyl Tellurium5 Under nitrogen, 0.29 g (0.70 mmol) of diphenyl ditellurium are reduced with 0.03 g (0.73 mmol) of sodium borohydride in 5 ml of hexamethylphosphoric triamide at 70-80° with stirring for 0.5 h. Then 0.14 g (0,73 mmol) of copper(l) iodide are added whereupon the mixture turns black. 0.18 g (0.73 minol) of l-iodo-2-nitrobenzene are added and the mixture is stirred well and heated at 80 90° for 1.5 h. The mixture is cooled, water is added, the whole is extracted with diethyl ether, the extract is washed with concentrated sodium chloride solution, and the organic layer is dried with anhydrous sodium sulfate. The solvent is evaporated under vacuum and the residue is chromatographed on a short column of alumina with hexane as eluent. Fractions containing the product are combined and evaporated to dryness and the residue is rccrystallized from ethanol yield 0.22 g (95%) m.p. 94°. 

Triphenylamine-o-arsinic acid is obtained when o-arsanilic acid, bromoDenzene and potassium carbonate are heated together in amyl alcohol in the presence of copper powder and cuprous iodide at 160° to 170° C. If this reaction is carried out at 180° to 140° C. only diphenyl-aniine-o-arsinic acid results. If p-dibroinobenzene is used in the condensation, the corresponding bromo-substituted triphenylamine-o-arsinic acid results. 

Cuprous phenyl, CuPhU—Cuprous iodide is added to a cold solution of magnesium phenyl bromide in ether. Complete solution takes place, and after a time the cuprous phenyl separates out as a white powder. It decomposes at 80° C. and when warmed with benzene is converted quantitatively into diphenyl and metallic copper, the latter appearing as a mirror. With water, benzene and cuprous oxide are formed, and with dilute nitric acid it is changed to nitrobenzene, concentrated nitric acid causing the compound to explode. Cuprous phenyl blackens in a few days, even when kept in a vacuum. 

ALKENES Allyl dimethyldithiocarbamate. Bis(t -cyclopentadienyl)niobium trihydride. Cyanogen bromide. Di-n-butylcopperlithium. a,o-Dichloromethyl methyl ether. 2,3-Dimethyl-2-butylborane. N,N-Dimethyl dichlorophosphoramide. Diphenyl diselenide. Di-n-propylcopperlithium. Ferric chloride. Grignard reagents. Iodine. Lithium phenylethynolate. Lithium 2,2,6,6-tetramethylpiperidide. Methyl iodide. o-Nitro-phenyl selenocyanate. Propargyl bromide. rra s-l-Propenyllithium. Selenium. Tetrakis(triphenylphosphine)palladium. Titanium(IH) chloride. Titanium trichloride-Lithium aluminum hydride. p-Toluenesulfonylhydrazine. Triphenylphosphine. Vinyl-copper reagents. Vinyllithium. Zinc. 

Silylcupration of Alkynes. Silylcupration of alk)mes may be made catalytic in copper by treating the silyllithium reagent with methylmagnesium iodide, followed by adding a catal)hic amount of copper(I) cyanide. The regiochemistry with terminal acetylenes is unimpaired, and the intermediate vinyl copper species reacts efficiently with allyl diphenyl phosphate. 

Chaudhari et al. reported encapsulation of copper complexes in zeolite-Y and MCM-41 or by tethering of copper complexes on various supports like zeolite-Y, silica, charcoal, or clay [87]. These materials were then characterized by a plethora of sophisticated analytical techniques like EPR, diffused reflectance UV-vis, XRD, IAS, ICPES, SEM, and TEM and employed for the amination of aryl iodide to synthesize diphenyl aniline or triphenyl amine (Scheme 21). 

X-ray structures) copper precatalysts have been isolated from ////-bis(diphenyl-phosphino)amme ligands and CuCl. Wan and co-workers [144, 145], proposed a system with the ability to couple aryl or heteroaiyl iodides with a bountiful variety of alkyl amines (Scheme 9). For these reactions, the authors also used a phosphoms ligand (phosphoramidite L23) with CuBr in DMF. 

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