Copper cyanide, and

A further improvement in the cuprate-based methodology for producing PGs utilizes a one-pot procedure (203). The CO-chain precursor (67) was first functionalized with zirconocene chloride hydride ia THF. The vinyl zirconium iatermediate was transmetalated direcdy by treatment with two equivalents of / -butyUithium or methyUithium at —30 to —70° C. Sequential addition of copper cyanide and methyUithium eUcited the /V situ generation of the higher order cyanocuprate which was then reacted with the protected enone to give the PG. 

The TiVC) coordinated organocopper compounds 260 and 261 were obtained from 2-lithiothiophene and copper cyanide and iodide, respectively (990M1571). 

Renal Effects. The information regarding renal effects following dermal exposure to cyanide in humans is limited to one case report. Transitory oliguria (scanty urination) was observed in a patient who accidentally fell into a cistern containing 1,000 gallons of hot copper cyanide and remained there for 3 minutes before being rescued (Dodds and McKnight 1985). 

Copper(l) cyanide is used in copper plating of nickel, chromium, zinc alloys, steel, and other metals or alloys. Such copper plating imparts brightness, smoothness, hardness, and strength. The cyanide solution employed for copper electroplating consists of copper cyanide and sodium cyanide. Other apph-cations of this compound are as an insecticide, a catalyst in polmerization, and as an antifouling agent in marine paints. 

A reaction flask was charged with 2-bromo-3-dodecylthiophene (81 mmol) and excess copper cyanide and the product obtained in 34% yield. 

The excess of copper cyanide and the use of a polar, high-boiling point solvent makes the purification of the products difficult. In addition, elevated temperatures (up to 200°C) lower the functional group tolerance. The use of alkali metal cyanides or cyanation reagents such as cyanohydrins, a catalytic amount of copper(I) iodide and kalium iodide, allows a mild, catalytic cyanation of various aryl bromides. 

Chemical oxidation is very effective in destroying free cyanide as well as cadmium, copper, and zinc cyanide complexes. However, nickel cyanide is incompletely destroyed, and iron cyanide complexes are apparently unaffected by chlorine or ozone. The ozone-UV radiation process (i.e., advanced oxidation process) is effective for treatment of complexed cyanide, such an ferric cyanide, copper cyanide, and nickel cyanide. Performance data of oxidation processes from the following industries are presented in the appendixes ... 

Properties White, crystalline double salt of copper cyanide and potassium cyanide copper content min 25.8% free potassium cyanide 1.25-3.0%. 

Properties White, crystalline, double salt of copper cyanide and sodium cyanide. D 1.013 (20C), decomposes at 100C. Soluble in water. 

Other procedures for the preparation of 2,4-dimethoxy-luuizonitrile include the reaction of 2,4-dimethoxybenzamide with thionyl chloride, the action of acetic anhydride on 2,4-dirnethoxybenzaldoxime, the reaction of diazotized 2,4-copper cyanide, and the acstion of cyanogen bromide on resorcinol dimethyl ether in the presence of aluminum chloride. ... 

KIS/CUP] Kisova, L., Cuprova, Equilibrium in aqueous solutions containing complex nickel and copper cyanides and free potassium cyanide, Collect. Czech. Chem. Commun., 24, (1959), 862-868, in German. Cited on pages 227,292, 293. 

Much work has been devoted to the reduction of smoke production from burning PVC. A large variety of compounds have been patented as smoke suppressors both for rigid and plasticized PVC, for example ferrocene, iron oxides, alumina trihydrate, molybdenum oxide, vanadium oxide, copper cyanide and thiocyanide. 

A variety of benzoxazoles (214) have been shown to selectively undergo copper-catalyzed direct ring-opening N-arylation over C-2 arylation when the coupling with aryl iodide (215) is conducted in a screw-capped vial rather than the standard round-bottomed flask (2015JOC3670). Two catalysts, copper cyanide and cyano bis(triphenylphosphine)copper(l), proved effective in generating the ring-opened products but displayed no activity with benzimidazoles and benzothiazoles. 

A proper choice of the catalyst allows the extension of the coupling to aryl iodides.107 Yields are satisfactory with para substituted electrophiles, less convenient with the ortho isomers. Further extension was obtained by replacing the palladium catalyst by copper cyanide, and the coupling reaction proceeds without sonication. The copper-zinc mixed reagent is able to couple with allylic... 

As mentioned earlier, one of the most significant applications of a-lithiation chemistry has been its utility in a-arylations. Dieter and Li have extended the a-arylation method to racemic 2-lithio-N-Boc piperidines using the combination of copper cyanide and palladium(O), albeit with the same substrate scope as noted for pyrrolidines vide supra). Coldham and Leonori applied the Negishi protocol to AT-Boc piperidine which gave access to a wider range of racemic 2-arylpiperidines (Scheme 11.33). ... 

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