Hydrogen cyanide lithium

High yields of optically active cyanohydrins have been prepared from hydrogen cyanide and carbonyl compounds using an enzyme as catalyst. Reduction of these optically active cyanohydrins with lithium aluminum hydride in ether affords the corresponding substituted, optically active ethanolamine (5) (see Alkanolamines). 

Acetone cyanohydrin nitrate will not nitrate amines with branching on the carbon a to the nitrate group. For these substrates the use of ethyl nitrate and lithium bases is favoured. a-Aminonitriles are frequently observed as impurities under the reaction conditions because of the slow decomposition of acetone cyanohydrin nitrate to hydrogen cyanide and acetone. The need for an excess of amine during these reactions is wasteful and only practical if this component is cheap and widely available. Other cyanohydrin nitrates are less efficient N-nitrating agents. ... 

Mecamylamine Mecamylamine, M2,3,3-tetramethylnorboman-2-ylamine (14.2. 2), is synthesized from 2,3,3-trimethylnorbomen-2, which is reacted in a Ritter reaction conditions with hydrogen cyanide in concentrated snlfuric acid, giving 2,3,3-trimethylnorbor-nan-2-ylformylamine (14.2.1), the reduction of which by lithium aluminum hydride leads to mecamylamine (14.2.2) [32,33]. 

By contrast, addition of hydrogen cyanide to J -pyrrolines yields stable nitriles, which are reduced by lithium aluminum hydride to diamines and can be saponified to acids318 (Scheme 14). 

Trimethylsilyl cyanide has been prepared in modest yield by the action of hexamethyldisilazane on hydrogen cyanide8 and the reaction of silver cyanide with trimethylchlorosilane.6,7 It has been prepared in good yield by the treatment of preformed lithium cyanide (from LiH and HCN) with trimethylchlorosilane in ether.7 The procedure described here not only affords trimethylsilyl cyanide in good yield, but also avoids the use of hydrogen cyanide and the need for Schlenk ware. 

In the reaction of butyllithium or lithium di-isopropylaminc with the Mannich bases derived from hydrogen cyanide, phosphine oxides, and phosphorous esters, as well as from phenols, jhc metal atom is prevalently bound to the CH2—N moiety (313 in big. 119, route b). This intermediate is then allowed to react with halides, epoxides, and other alkylating reagents in order to link an alkyl group to methylene. Under proper conditions, aldehydes, ketones and enamines can be prepared by this method. 

Tetrahydropyridazines with unsubstituted NH groups behave as secondary amines the double bond has been hydrogenated with lithium aluminum hydride and addition of hydrogen cyanide is known. Oxidation of 3,6-diphenyl-1,4,5,6-tetrahydro-pyridazine with lead dioxide results in aromatization. ... 

SAFETY PROFILE A highly corrosive irritant to the eyes, skin, and mucous membranes. Mildly toxic by inhalation, Explosive reaction with alcohols + hydrogen cyanide, potassium permanganate, sodium (with aqueous HCl), tetraselenium tetranitride. Ignition on contact with aluminum-titanium alloys (with HCl vapor), fluorine, hexa-lithium disilicide, metal acetylides or carbides (e.g., cesium acetylide, rubidium ace-tylide). Violent reaction with 1,1-difluoro-ethylene. Vigorous reaction with aluminum, chlorine + dinitroanilines (evolves gas). Potentially dangerous reaction with sulfuric acid releases HCl gas. Adsorption of the acid onto silicon dioxide is exothermic. See also HYDROGEN CHLORIDE (AEROSOL) and HYDROCHLORIC ACID. 

Dichloro(l, 3-propanediyl)platinum and its bis(pyridine) derivative have been studied by a number of authors. Dichloro(l,3-propanediyl)platinum, and the corresponding substituted 1,3-propanediyl platinum compounds release the parent cyclopropane on treatment with potassium cyanide, potassium iodide, a tertiary phosphine, carbon monoxide, and other ligands.2,6 Reduction by means of hydrogen or lithium aluminum hydride yields chiefly isomeric substituted propanes. Dichlorobis(pyridine)(l,3-propanediyl)platinum in refluxing benzene yields a pyridinium ylid complex, - (CH3CH2CHNC5Hs)-PtpyCla. 

ASYMMETRIC SYNTHESIS Diboiane. Diisopinocamphenylborane. Hydrogen cyanide. (-) and (+)-2,3-0-Isopropylidene-2,3-dihydroxy-l,4-bis(diphenylphosphino)-bntane. (+)- R)-/r ns- 3-Styryl-p-tolyl sulfoxide. p-Tolylsulfinylcaibonion lithium salt. 

Theoretical description of the hydrogen cyanide-hydrogen isocyanide and lithium cyanide-lithium isocyanide isomerization using the FSGO method. ... 

The reagent is prepared by reaction of lithium borohydride with liquid hydrogen cyanide in ether and isolated as the dioxane complex. It is remarkably stable to... 

The reaction of ( )-3,3-dimethyl-l-butene-l,2-r/2 with hydrogen cyanide and of ( )-3,3-dimethyl-l-butene-l-d2 with deuterium cyanide stereospecifically proceeds in a cis fashion with Pd(Diop)2 used as the catalyst precursor20,24. The stereochemistry of the products is verified by NMR and characterization of the thiourea derivatives of the corresponding amine obtained with lithium aluminum deuteride. No //wu-addition products exceeding a limit of 5-10% can be detected. 

CHLOROACETONITRILE or o-CHLOROACETONITRILE or 2-CHLOROACETONITRILE (107-14-2) ClCHjCN Forms explosive mixture with air (flash point 133°F/56°C Fire Rating 2). Contact with water, steam, or strong acid, or acid fumes produce toxic hydrogen cyanide gas. Violent reaction with strong oxidizers. Incompatible with sodium nitrate, lithium alanate. Thermal decomposition releases toxic hydrogen cyanide and hydrogen chloride gas. On small fires, use dry... 

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