Diethylaluminium cyanide

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Diethylaluminium cyanide

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Molar mass	Template:Chem molar mass
Appearance	Dark brown, clear liquid (1.0 mol/L in toluene)
Density	0.864 g/cm3 at (25 °C) (liquid)
Boiling point	Template:Chembox CalcTemperatures
Solubility	Benzene, Toluene, diisopropyl ether

Diethylaluminium cyanide ("Nagata's reagent") is the organoaluminium compound with formula Template:Chem2. This colorless compound is usually handled as a solution in toluene. It is a reagent for the hydrocyanation of α,β-unsaturated ketones.

Synthesis

Diethylaluminium cyanide was originally generated by treatment of triethylaluminium with a slight excess of hydrogen cyanide. The product is typically stored in ampoules because it is highly toxic. It dissolves in toluene, benzene, hexane and isopropyl ether. It undergoes hydrolysis readily and is not compatible with protic solvents.

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Structure

Diethylaluminium cyanide has not been examined by X-ray crystallography, although other diorganoaluminium cyanides have been. Diorganylaluminium cyanides have the general formula Template:Chem2, and they exist as cyclic trimers (n = 3) or tetramers (n = 4). In these oligomers, one finds AlCN---Al linkages. One compound similar to diethylaluminium cyanide is bis[di(trimethylsilyl)methyl]aluminium cyanide, Template:Chem2, which has been shown crystallographically to exist as a trimer with the following structure:

trimeric bis[di(trimethylsilyl)methyl]aluminium cyanide

Bis(tert-butyl)aluminium cyanide, Template:Chem2 exists as a tetramer in the crystalline phase:

tetrameric bis(tert-butyl)aluminium cyanide

Uses

Diethylaluminium cyanide is used for the stoichiometric hydrocyanation of α,β-unsaturated ketones. The reaction is influenced by the basicity of the solvent. This effect arises from the Lewis acidic qualities of the reagent. The purpose of this reaction is to generate alkylnitriles, which are precursors to amines, amides, carboxylic acids esters and aldehydes.

File:Diethylaluminumcyanidehydrocyanation.png

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