Sodium metal reactions with

Reactions. Phosgene interacts with many classes of inorganic and organic reagents. The reactions have been described extensively (10). Reaction with sodium metal takes place at room temperature, but reaction with 2inc requires warming. 

Iprindol (25) is yet another antidepressant drug that differs structurally from the classical tricyclic antidepressants. Condensation of phenylhydrazine and cyclooctanone by the Rogers-Corson modification of the Fischer indole synthesis affords the tricyclic intermediate, 24. The active hydrogen of 6,7,8,9,10-hexahydro-5H-cyclooct[b]indole (24) is removed by reaction with sodium metal in DMF and the resulting salt condensed with 3-dimethylaminopropyl chloride. There is thus obtained iprindol (25). ... 

Reaction with sodium. Metallic sodium reacts with alcohols with the evolution of hydrogen. 

The alkoxide ion nucleophile is often prepared from the alcohol by reaction with sodium metal, as shown in the following equation for the formation of ethoxide ion from ethanol ... 

I.3.I.2.2. By Reaction with Sodium Metal and Other Reducing Agents... 

Charles et al. 11661 used TM to study the reduction of Fe3C with excess lithium or sodium metal. Decomposition of Fe3C, shown in Figure 11.45, is rapid above 600"C. whereas the reaction with sodium metal indicates that no direct reaction such as... 

This organopotassium reagent is obtained as a grey suspension by reaction of bis(trimethylsilylmethyl)mercury (Fluka) with potassium/sodium alloy (5 1 by weight) in pentane for 30 min. A similar reaction with sodium metal is slower. ... 

Diethyl malonate on reaction with sodium metal gives rise to sodium malonic ester which on treatment with ethyl bromide results into the formation of diethyl ester of ethyl malonic acid with the elimination of hydrobromic acid. The resulting ester on further reaction with 2-bromopentane gives the desired eompound, i.e., diethyl ester of ethyl (1-methyl butyl) malonic acid which on subsequent treatment with thiourea forms thiopental with the elimination of two moles of ethanol. Ultimately, the enol-iorm of thiopental when reaeted with a ealeulated amoimt of sodium hydroxide, it gives thiopental sodium. 

The following is the mass spectmm of compound C, C3H3O. Compound C is infinitely soluble in water, undergoes reaction with sodium metal with the evolution of a gas, and undergoes reaction with thionyl chloride to give a water-insoluble chloroaUcane. Propose a structural formula for compound C and write equations for each of its reactions. 

The reaction of a carbanion with ethyl chloroformate incorporates an ester group directly into a molecule. Amino-alkyne 1.172 was converted to an amino-ester via reaction with sodium metal to give the alkyne anion and then with ethyl chloroform-... 

The Wurtz reaction is the reaction with sodium metal as shown in eq. (10.5). One disadvantage is that large volumes of solvent have to be used to suppress the... 

In 1990, loo and coworkers reported the conversion of l,l-dichloro-2,3,4,5-tetraphenyl-1-silacyclopentadiene to the disodium salt by reaction with sodium metal. ... 

In the reaction with hydrogen halides, the C—O bond in the alcohol breaks. However, in some other reactions the O—H bond in the alcohol breaks. The reaction with sodium metal is an example ... 

Sodium ethoxide is prepared by the reaction of sodium metal with ethanol... 

These reactions are usehil for the preparation of homogeneous difunctional initiators from a-methylstyrene in polar solvents such as tetrahydrofuran. Because of the low ceiling temperature of a-methylstyrene (T = 61° C) (26), dimers or tetramers can be formed depending on the alkaU metal system, temperature, and concentration. Thus the reduction of a-methylstyrene by sodium potassium alloy produces the dimeric dianionic initiators in THF (27), while the reduction with sodium metal forms the tetrameric dianions as the main products (28). The stmctures of the dimer and tetramer correspond to initial tail-to-tail addition to form the most stable dianion as shown in equations 6 and 7 (28). 

The speed of the reaction depends both on the metal and on the alcohol, increasing as electropositivity iacreases and decreasiag with length and branching of the chain. Thus sodium reacts strongly with ethanol, but slowly with tertiary butyl alcohol. The reaction with alkaU metals is sometimes carried out ia ether, ben2ene, or xylene. Some processes use the metal amalgam or hydride iastead of the free metal. Alkaline earth metals and aluminum are often covered with an oxide film which hinders the reaction. 

The reaction is displaced to the right by dissociation of sodium hydride and Hberation of hydrogen. This dissociation is favored under vacuum or when the reaction 2one is swept with an inert gas to remove the hydrogen (24,25). In this manner, sodium monoxide substantially free of sodium and sodium hydroxide is produced. In the more compHcated reaction between sodium metal and anhydrous potassium hydroxide, potassium metal and sodium hydroxide are produced in a reversible reaction (42,43) ... 

A process development known as NOXSO (DuPont) (165,166) uses sodium to purify power plant combustion flue gas for removal of nitrogen oxide, NO, and sulfur, SO compounds. This technology reHes on sodium metal generated in situ via thermal reduction of sodium compound-coated media contained within a flue-gas purification device, and subsequent flue-gas component reactions with sodium. The process also includes downstream separation and regeneration of spent media for recoating and circulation back to the gas purification device. A full-scale commercial demonstration project was under constmction in 1995. 

Chrome dyes are acid dyes (mol wt 300—600) that contain groups capable of forming complexes by reaction with a metal salt, usually sodium or potassium dichromate (94,97). The chrome/dye complex has lower solubiUty, and hence better wetfastness, than the parent dyestuff. Reaction between the... 

Two classes of charged radicals derived from ketones have been well studied. Ketyls are radical anions formed by one-electron reduction of carbonyl compounds. The formation of the benzophenone radical anion by reduction with sodium metal is an example. This radical anion is deep blue in color and is veiy reactive toward both oxygen and protons. Many detailed studies on the structure and spectral properties of this and related radical anions have been carried out. A common chemical reaction of the ketyl radicals is coupling to form a diamagnetic dianion. This occurs reversibly for simple aromatic ketyls. The dimerization is promoted by protonation of one or both of the ketyls because the electrostatic repulsion is then removed. The coupling process leads to reductive dimerization of carbonyl compounds, a reaction that will be discussed in detail in Section 5.5.3 of Part B. 

Acetylenes are sufficiently acidic to react with sodium metal to generate acetylides, useful nucleophiles in the formation of carbon-carbon bonds. The reaction is classically carried out in liquid ammonia, which is a good solvent for alkali metals but which is troublesome to handle. Two convenient modifications of the acetylide generation reaction overcome this difficulty and are discussed below along with the classical method. 

The reaction of sodium metal with O2 gas produces a crust of sodium peroxide, which blocks additional... 

The reaction of sodium metal with molecular chlorine gas to produce solid sodium chloride can be analyzed by breaking the overall process into a series of steps involving ions in the gas phase. 

C21-0090. The first commercially successful method for the production of aluminum metal was developed in 1854 by H. Deville. The process relied on earlier work by the Danish scientist H. Oersted, who discovered that aluminum chloride is produced when chlorine gas is passed over hot aluminum oxide. Deville found that aluminum chloride reacts with sodium metal to give aluminum metal. Write balanced equations for these two reactions. 

Tri-(l-naphthyl)phosphine is cleaved by alkali metals in THF solution. " Reaction with sodium gives the naphthalene radical-ion, with lithium the perylene radical-ion, and with potassium the radical-ion (22). Hydrocarbon radical-ion formation was thought to occur via naphthalene derived from the metal naphthalenide. E.s.r. spectra of further examples of phosphorus-substituted picrylhydrazyl radicals have been reported. ... 

The unsoluble fluorophosphates can be prepared from the sodium salt by reaction with heavy metal nitrates, whereas the watersoluble salts are appropriately prepared by the reaction of the sligthly soluble AgjPOjF with heavy metal chlorides (24). Acid salts M H[P03F] with = Na, K, NH4 result from fractional precipitation by addition of alcohol and ether to the aqueous solution of the free acid (17). Further methods for the synthesis of fluorophosphates are given by Eqs. (12) and (13), which lead to dimethylin fluorophosphate (32) and to tin (II) difluorophosphate (55) ... 

Another important reductive coupling is the conversion of esters to a-hydroxyketones (acyloin condensation).267 This reaction is usually carried out with sodium metal in an inert solvent. Good results have also been obtained for sodium metal dispersed on solid supports.268 Diesters undergo intramolecular reactions and this is also an important method for the preparation of medium and large carbocyclic rings. 

Poly(silylene) polymers are usually made by the reaction of diorganodichlorosilanes with sodium metal, in an inert diluent at temperatures above 100°C. (11.) Rapid stirring is ordinarily used so that the sodium is finely dispersed, speeding the rate of reaction. Either homopolymers or copolymers can be synthesized ... 

A vigorous reaction occurs on heating DMF with sodium metal. 

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