Alkyl halides Aluminum iodide

Aluminum iodide, 17 of alkyl halides by sulfur nucleophiles 1 -(2-Hydroxyethyl) -4,6-diphenylpyri-dine-2-thione, 146... 

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... 

No reaction of unmilled aluminum powder with alkyl halides was observed during 10 hours of contact. When aluminum was milled with stainless steel balls in a stainless steel pot under helium at room temperature in the presence of butyl iodide for 8 min, an exothermic reaction was initiated and no more activation was required for the continuation of the reaction. 

Halides and tosylates. Trevoy and W. G. Brown found that lithium aluminum hydride reduces benzyl iodide and benzyl bromide in high yield at 35° in either diethyl ether or tetrahydrofurane. In tetrahydrofurane at 65°, benzyl chloride and 1 -bromodecane are reduced to toluene and to n-decane, both in 72% yield. Johnson, Blizzard, and Carhart found that lithium aluminum hydride reacts more sluggishly than in other reductions and presented experimental evidence that not all four hydrogen atoms possess adquate reactivity toward alkyl halides. Thus the reaction probably proceeds in at least two steps, the first of which is much more rapid than... 

It has hitherto been assumed that only aryl iodides react with aluminum to form the corresponding aryl aluminum sesqui iodides (246). It has now been found, however, that aryl chlorides and bromides also react with aluminum. The latter are activated by dry milling at room temperature in the presence of aluminum chloride (260). Use of aluminum chloride is not essential if the reactants are brought together directly in a vibratory mill at an elevated temperature (ca. 100°C) in chlorobenzene (171). As in the case of alkyl halides and aluminum, an equimolar mixture of aryl aluminum dihalide and diaryl aluminum halide results ... 

The reactions of hexaorganodileads with nitric acid 358,359), dimethyl-acetic acid 358), magnesium/magnesium iodide 296), aluminum chloride 349, 360), and alkyl halides 280,361, 362) also result in Pb—Pb cleavage. Reaction of hexaethyldilead with sulfuryl chloride, thionyl chloride, sulfur dichloride, and sulfur monochloride has been reported (363). The yield of triethyllead chloride was observed to decrease with increasing nucleophilic character of the sulfur atom, in the order listed above. 

A thio-substituted, quaternary ammonium salt can be synthesized by the Michael addition of an alkyl thiol to acrylamide in the presence of benzyl trimethyl ammonium hydroxide as a catalyst [793-795]. The reaction leads to the crystallization of the adducts in essentially quantitative yield. Reduction of the amides by lithium aluminum hydride in tetrahydrofuran solution produces the desired amines, which are converted to desired halide by reaction of the methyl iodide with the amines. The inhibitor is useful in controlling corrosion such as that caused by CO2 and H2S. 

Primary and secondary alkyl bromides, iodides, and sulfonates can be reduced to the corresponding alkanes with LiBHEt3 (superhydride) or with lithium aluminum hydride (LiAlH4, other names lithium tetrahydridoaluminate or lithium alanate). If such a reaction occurs at a stereocenter, the reaction proceeds with substantial or often even complete stereoselectivity via backside attack by the hydride transfer reagent. The reduction of alkyl chlorides to alkanes is much easier with superhydride than with LiAlH4. The same is true for sterically hindered halides and sulfonates ... 

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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