Diphenyl copper chloride

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... 

The ligand 2-allylpyridine is reported to form chelate complexes with copper(I) chloride, silver nitrate and platinum(II) chloride (29). Diphenyl vinylphosphine also forms stable 1 1 and 2 1 adducts with silver nitrate in which both the phosphorous and the double bond are thought to be coordinated to silver (30). 

Diphenylacetic acid has been obtained by the reduction of benzilic acid with hydriodic acid and red phosphorus 1 by the treatment of phenylbromoacetic acid with benzene and zinc dust,2 or with benzene and aluminum chloride 3 by the hydrolysis of diphenylacetonitrile 4 by heating a-diphenyldichloroethyl-ene with alcoholic sodium ethylate 5 by heating benzilic acid 6 from diphenylmethane, mercury diethyl, sodium and carbon dioxide 7 by the oxidation of a,a,5,S-tetraphenyl- 8-butine 8 by the decomposition of some complex derivatives obtained from diphenylketene 9 by the hydrolysis of diphenyl-5,5-hydan-toin 10 by the treatment of diphenylbromoacetic acid with copper 11 by the oxidation of dichlorodiphenylcrotonic acid.12... 

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... 

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°. 

Bis[4-methoxyphenyl] tellurium, obtained from 4-methoxybenzene and tellurium tetrachloride and reduction of the resultant bis[4-methoxyphenyl] tellurium dichloride, was converted to methyl 4-methoxybenzoate in 99% yield1. Methyl benzoate was similarly obtained from diphenyl tellurium in yields higher than 90%. These reactions can be carried out with catalytic amounts of palladium(II) chloride when copper(II) chloride is used as an oxidant1. 

The Michael addition of organometallic nucleophiles to enones in the presence of copper(I) salts produces enolates which on treatment with phenylselenenyl bromide give a-seleno ketones. For example, the reaction of the zirconium enolate of 15 with a mixture of phenylselenenyl bromide and diphenyl diselenide affords a mixture of diastereomeric (2R)- and (2V)-phenylse-leno)cyclopentanones 16 in 50% and 31 % isolated yield, respectively12. The analogous reaction with phenylselenenyl chloride gives only the tram-isomer in 27% yield formation of the cw-product is not observed12. 

Pd2(DBA)3/BINAP system (DBA = dibenzylideneacetone BINAP = 2,2-bis(diphenyl-phosphanyl)-l,1-binaphthyl). Best results were obtained using electron-deficient aryl bromides. Aryl chlorides of any type, however, failed to react under these conditions. The aryl-aziridine coupling reaction could also be carried out with arylboronic acids using a copper catalyst (Scheme 55) <2003JOC2045>. 

Unlike diphenyl chloroarsine, phenarsazine chloride attacks iron, steel, bronze and copper. 

Chloro-3-hydroxy-5(and 6)-methylpyrazine with ammonium hydroxide, copper, and cupric chloride at 125° for 15 hours gave 2-amino-3-hydroxy-5(and 6)-methylpyrazine (373, 835), but 2-chloro-5-hydroxy-3,6-dimethylpyrazine was recovered unchanged after treatment with alcoholic ammonia under drastic conditions (312) and 2-chloro-3-hydroxy-5,6-diphenylpyrazine with pyridine and its hydrochloride at reflux gave the betaine (33) from 2-hydroxy-5,6-diphenyl-3-pyridiniopyrazine chloride (863). Replacement of the chloro substituent occurred... 

A number of triphenylbismuthonium diacylylides and also the diphenylsulphonylylide undergo transylidation when treated with dimethyl sulphide in the presence of copper(I) chloride in benzene at room temperature, giving the corresponding dimethylsulphonium ylides no such reaction took place with diphenyl sulphide Some of these bismuthonium ylides reacted with triphenylarsine or triphenylphosphine and were converted thereby into arsonium or phosphonium ylides they did not react with triphenylstibine L The conversion of the diacetylylide into the 4,4-dimethyl-2,6-dioxocyclohexylide as mentioned in Section IX.A should also be noted. 

Reducing agents Aluminum hydride. Bis-3-methyl-2-butylborane. n-Butyllithium-Pyridine. Calcium borohydride. Chloroiridic acid. Chromous acetate. Chromous chloride. Chromous sulfate. Copper chromite. Diborane. Diborane-Boron trifluoride. Diborane-Sodium borohydride. Diethyl phosphonate. Diimide. Diisobutylaluminum hydride. Dimethyl sulfide. Hexamethylphosphorous triamide. Iridium tetrachloride. Lead. Lithium alkyla-mines. Lithium aluminum hydride. Lithium aluminum hydride-Aluminum chloride. Lithium-Ammonia. Lithium diisobutylmethylaluminum hydride. Lithium-Diphenyl. Lithium ethylenediamine. Lithium-Hexamethylphosphoric triamide. Lithium hydride. Lithium triethoxyaluminum hydride. Lithium tri-/-butoxyaluminum hydride. Nickel-aluminum alloy. Pyridine-n-Butyllithium. Sodium amalgam. Sodium-Ammonia. Sodium borohydride. Sodium borohydride-BFs, see DDQ. Sodium dihydrobis-(2-methoxyethoxy) aluminate. Sodium hydrosulflte. Sodium telluride. Stannous chloride. Tin-HBr. Tri-n-butyltin hydride. Trimethyl phosphite, see Dinitrogen tetroxide. 

---