Diethylaluminum cyanide ("Nagata's reagent") is the

organoaluminum compound Organoaluminium chemistry is the study of compounds containing bonds between carbon and aluminium. It is one of the major themes within organometallic chemistry. Illustrative organoaluminium compounds are the dimer trimethylaluminium, the monomer ...

with formula ((C₂H₅)₂AlCN)_n. This colorless compound is usually handled as a solution in toluene. It is a

reagent In chemistry, a reagent ( ) or analytical reagent is a substance or compound added to a system to cause a chemical reaction, or test if one occurs. The terms ''reactant'' and ''reagent'' are often used interchangeably, but reactant specifies a ...

for the

hydrocyanation In organic chemistry, hydrocyanation is a process for conversion of alkenes to nitriles. The reaction involves the addition of hydrogen cyanide and requires a catalyst. This conversion is conducted on an industrial scale for the production of ...

of α,β-unsaturated

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

Synthesis

Diethylaluminum cyanide was originally generated by treatment of

triethylaluminum Triethylaluminium is one of the simplest examples of an organoaluminium compound. Despite its name it has the formula Al2( C2H5)6 (abbreviated as Al2Et6 or TEA), as it exists as a dimer. This colorless liquid is pyrophoric. It is an industrially ...

with a slight excess of

hydrogen cyanide Hydrogen cyanide, sometimes called prussic acid, is a chemical compound with the formula HCN and structure . It is a colorless, extremely poisonous, and flammable liquid that boils slightly above room temperature, at . HCN is produced on an ...

. The product is typically stored in ampoules because it is highly toxic. It dissolves in

toluene Toluene (), also known as toluol (), is a substituted aromatic hydrocarbon. It is a colorless, water-insoluble liquid with the smell associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) at ...

benzene Benzene is an organic chemical compound with the molecular formula C6H6. The benzene molecule is composed of six carbon atoms joined in a planar ring with one hydrogen atom attached to each. Because it contains only carbon and hydrogen atoms, ...

hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...

and isopropyl ether. It undergoes

hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...

readily and is not compatible with

protic solvents In chemistry, a protic solvent is a solvent that has a hydrogen atom bound to an oxygen (as in a hydroxyl group ), a nitrogen (as in an amine group or ), or fluoride (as in hydrogen fluoride). In general terms, any solvent that contains a labile ...

. :Et₃Al + HCN → 1/n (Et₂AlCN)_n + EtH

Structure

Diethylaluminum cyanide has not been examined by

X-ray crystallography X-ray crystallography is the experimental science determining the atomic and molecular structure of a crystal, in which the crystalline structure causes a beam of incident X-rays to diffract into many specific directions. By measuring the angles ...

, although other diorganoaluminum cyanides have been. Diorganylaluminum cyanides have the general formula (R₂AlCN)_''n'', and they exist as cyclic trimers (''n'' = 3) or tetramers (''n'' = 4). In these oligomers, one finds AlCN---Al linkages. One compound similar to diethylaluminum cyanide is bis /nowiki>di(trimethylsilyl)methylluminium cyanide, ((Me₃Si)₂CH)₂AlCN, which has been shown crystallographically to exist as a trimer with the following structure: : Cyclo-(((Me3Si)2CH)2AlCN)3-2D

Bis(''tert''-butyl)aluminium cyanide, ^''t''Bu₂AlCN exists as a tetramer in the crystalline phase: : Cyclo-(tBu2AlCN)4-2D

Uses

Diethylaluminum cyanide is used for the stoichiometric

of α,β-unsaturated ketones. The reaction is influenced by the

basicity In chemistry, there are three definitions in common use of the word base, known as Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. ...

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. : Diethylaluminumcyanidehydrocyanation

References

External links

* {{Aluminium compounds Cyanides Organoaluminium compounds