Sodium aluminum hydride alkyl halides

Alkyl azides prepared by nucleophilic substitution of alkyl halides by sodium azide as shown m the first entry of Table 22 3 are reduced to alkylammes by a variety of reagents including lithium aluminum hydride... 

Tributyltin hydride, 316 Zinc iodide, 280 From alkyl halides Lithium aluminum hydride-Ceri-um(III) chloride, 159 Palladium catalysts, 230 Sodium cyanoborohydride-Tin(II) chloride, 280 From alkyl sulfonates Lithium triethylborohydride, 153 From thiols... 

Reduction of halides. Primary, secondary, and certain tertiary halides and tosylates can be selectively reduced by sodium borohydride in DMSO or sulfolane. 1,2-Dibromides are reduced to hydrocarbons in moderately good yields. The method complements that of Bell and Brown,2 which uses sodium borohydride in 65% aqueous diglyme for reduction of secondary and tertiary alkyl halides which are capable of forming relatively stable carbonium ions (1, 1054). Lithium aluminum hydride reduction affords only olefins. Reduction of optically active tertiary alkyl halides proceeds with racemization, presumably by way of an elimination-addition mechanism.3... 

Hydride reagents (lithium aluminum hydride, LiAlHt, and sodium borohy-dride, NaBHt) are a source of the nucleophilic hydride species Hr. Reaction of hydride with a suitable carbon electrophile results in a reduction of that carbon (by increasing the number of C-H bonds). Reactions of carbonyl compounds with lithium aluminum hydride (LAH) generally give an alcohol product (after workup), with the exception of amides, which give amine products. Sodium borohydride is less reactive than LAH. It does not react with esters, amides, or carboxylic acids, so it is described as being selective for aldehydes and ketones. Sodium borohydride also fails to reduce nitroalkanes or alkyl halides, so LAH must be used in those reactions. 

Alkylation of Azide Ion and Reduction A much better method for preparing a primary amine from an alkyl halide is first to convert the alkyl halide to an alkyl azide (R—N3) by a nucleophilic substitution reaction, then reduce the azide to a primary amine with sodium and alcohol or with lithium aluminum hydride. 

NITROCARBOL (75-52-5) Forms explosive mixture with air (flash point 95°F/35°C). Thermally unstable. Shock, friction, pressure, or elevated temperature above 599°F/315°C can cause explosive decomposition, especially if confined. Violent reaction with strong oxidizers, alkyl metal halides, diethylaluminum bromide, formic acid, methylzinc iodide. Contact with acids, bases, acetone, aluminum powder, amines, bis(2-aminoethyl)amine, haolforms make this material more sensitive to explosion. Reacts, possibly violently, with ammonium hydroxide, calcium hydroxide, calcium hypochlorite, 1,2-diaminomethane, formaldehyde, hexamethylbenzene, hydrocarbons, hydroxides, lithium perchlorite, m-methyl aniline, nickel peroxide, nitric acid, metal oxides, potassium hydride, potassium hydroxide, sodium hydride. Mixtures with ammonia, aniline, diethylenetriamine, metal oxides, methyl amine, morpholine, phosphoric acid, silver nitrate form shock-sensitive compounds. Forms high-explosive compound with urea perchlorate. Mixtures with hydrocarbons and other combustible materials can cause fire and explosions. Attacks some plastics, rubber, and coatings. 

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