Copper I salt

Reactions that employ copper(I) salts as reagents for replacement of nitrogen m diazo mum salts are called Sandmeyer reactions The Sandmeyer reaction using copper(I) cyanide is a good method for the preparation of aromatic nitriles... 

The main by-products of the Ullmaim condensation are l-aniinoanthraquinone-2-sulfonic acid and l-amino-4-hydroxyanthraquinone-2-sulfonic acid. The choice of copper catalyst affects the selectivity of these by-products. Generally, metal copper powder or copper(I) salt catalyst has a greater reactivity than copper(Il) salts. However, they are likely to yield the reduced product (l-aniinoanthraquinone-2-sulfonic acid). The reaction mechanism has not been estabUshed. It is very difficult to clarify which oxidation state of copper functions as catalyst, since this reaction involves fast redox equiUbria where anthraquinone derivatives and copper compounds are concerned. Some evidence indicates that the catalyst is probably a copper(I) compound (28,29). 

A convenient route to A -isoxazoline N-oxides has been developed from nitrostyrenes using dimethylsulfoxonium methylide. The addition of the ylide (572) to the nitrostyrene (571) was greatly facilitated by the presence of copper(I) salts, the isoxazoline N-oxide (573) being obtained in excellent yield (76JOC4033). 

Metathesis of the trifluoromethylcadmium or tnfluoromethylzinc reagent with copper (I) salts gives solutions of trifluoromethylcopper [210] (equation 140). Depending on the stoichiometry and copper salt used, either CF3CU L or (Cp3)2Cu can be produced [211],... 

C. Cross-Coupling of Halogenopyrazoles with Terminal Acetylenes and Their Copper(I) Salts (Tables X to XV)... 

If the reaction of diacetylene and its substituted derivatives with ammonia or primary amines is carried out in the presence of a copper(I) salt, the main reaction product formed in an autoclave after brief heating to 150°C turns out to be pyrrole or pyrrole derivatives 1 (65CB98 71MI1). 

The Glaser coupling reaction is carried out in aqueous ammonia or an alcohol/ammonia solution in the presence of catalytic amounts of a copper-I salt. The required copper-II species for reaction with the acetylide anion R-C=C are generated by reaction with an oxidant—usually molecular oxygen. For the Eglinton procedure, equimolar amounts of a copper-II salt are used in the presence of pyridine as base. 

A variant for the synthesis of diaryl ethers—e.g. diphenyl ether 9, where an aryl halide and a phenoxide are reacted in the presence of copper or a copper-(I) salt, is called the Ullmann ether synthesis. ... 

Kupferozydul, n. cuprous oxide, copper(I) oxide, -hydrat, n. cuprous hydroxide, cop-per(I) hydroxide, -salz, n. cuprous salt, copper (I) salt, -verblndung,/. cuprous compound, copper(I) compound. 

The precipitate is curdy (compare silver chloride) and is readily coagulated by boiling. It is washed with dilute ammonium thiocyanate solution a little sulphurous acid or ammonium hydrogensulphite is added to the wash solution to prevent any oxidation of the copper)I) salt. 

Reaction of ( )-3-fcrt-Butjlcarbonyloxy-l-phenyl-l-butene (5) with Grignard Reagents Containing Copper(I) Salts General Procedure16 ... 

The synthesis and mechanism of formation of a triazene from an arenediazonium ion and an amine with one or two aliphatic substituents (see Scheme 13-1, R = alkyl, R = H or alkyl) will be discussed in Section 13.2. Here we will briefly mention Dimroth s method (1903, 1905 a) for synthesis of wholly aliphatic triazenes (Scheme 13-6, R and R = alkyl). Dimroth obtained these by the action of Grignard reagents on alkyl azides followed by isolation via copper(i) salts. The Grignard method can also be applied for the synthesis of triazenes with an aromatic substituent by using an aryl azide. 

Copper proteins, 1,168 5,720 models, 2,85 nonblue, 5,723 type 111, 5,724 Copper salts cellulose dyes, 6,38 Copper(I) salts stabilization, 6,786 Copper(II) salts ammoniacal leaching, 6,787 oxidant... 

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... 

Benzenesulfonyl chloride, 4-methyl- [p-Tol-uenesulfonyl chloride], 55, 57, 59 Benzenethiol [Phenol, thio-], 55, 122 Benzenethiol, copper(I) salt [Thiophenol, copper(I) salt], 55, 123 Benzenethiol, lithium salt [Thiophenol, lithium salt], 55, 1 22 Benzoic acid, 2-amino- [Anthramlic acid], p bromination of, 55, 23... 

Like all the coinage metals, copper forms compounds with oxidation number + 1. However, in water, copper(I) salts disproportionate into metallic copper and copper(II) ions. The latter exist as pale blue [Cu(H20)6]2+ ions in water. 

Wilson and Lyle [36] recently reported the synthesis and use of a new C2-symmetric 2,2 -bipyridyl ligand that answered these steric demands, since, associated to copper(I)salts, high diastereoselectivities and enantioselectivities trans/cis = 80/20 and 82% ee) could be achieved in the benchmark... 

Fe(OTf)2-catalyzed aziridination of enol silyl ethers with PhlNTs followed by ring opening led to a-N-tosylamido ketones in good yields (Scheme 27) [81]. With silyl ketene ketal (R = OMe) as substrate, the N-tosyl-protected amino acid ester was obtained in 50% yield. In contrast, the copper (I) salt CuClOq was found not effective for this substrate [82]. 

Cul, 12mol% of 2,2 -dipyridyl, in lOvol of xylene diglyme (9 1) at 140°C with azeotropic removal of the water as it was formed. The azeotropic removal of water helped alleviate the problem of solids coating the reaction vessel walls, which led to stalling of the reaction. The reaction was complete in less than lOh, typically with 96% assay yield and 92% isolated yield for 49 after aqueous work-up and subsequent crystallization [14b-d]. It was noteworthy that this catalytic system composed of the copper(I) salt with bipyridyl ligand was recently reported to be applicable to a wide range of Ullmann-type ether formations [14d]. 

Addition of RMgBr to nitriles. Grignard reagents react with nitriles slowly if at all, but even r-butylmagnesium chloride will add to nitriles in refluxing THF when catalyzed by a copper(I) salt. The adduct can be converted to a ketimine by anhydrous protonation, to a primary amine by reduction (Li/NH,), or to a ketone by hydrolysis. The actual reagent may be a cuprate such as R3Cu(MgX)2. 

The Sn2" substitution could be performed in the presence of a catalytic amount of a copper(I) salt [99]. The simultaneous addition of the substrate 112a and tBuLi to 10mol% tBu2CuLi-LiI in diethyl ether at -50 °C gave the vinylallene 114a in 90% yield as a 1 2 mixture of E- and Z-isomers (Scheme 3.58). 

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