Hydrocyanation

Hydrocyanation is, most fundamentally, the process whereby H+ and –CN ions are added to a molecular substrate. Usually the substrate is an alkene and the product is a nitrile. When –CN is a ligand in a transition metal complex, its basicity makes it difficult to dislodge, so, in this respect, hydrocyanation is remarkable. Since cyanide is both a good σ–donor and π–acceptor its presence accelerates the rate of substitution of ligands trans from itself, the trans effect.1 A key step in hydrocyanation is the oxidative addition of hydrogen cyanide to low–valent metal complexes. In hydrocyanation of unsaturated carbonyls addition over the alkene competes with addition over the carbonyl group.

Read more about HydrocyanationInorganic Chemistry, Usage, History

Other articles related to "hydrocyanation":

Nitrile - Synthesis - Hydrocyanation
... An example of hydrocyanation is the production of adiponitrile from 1,3-butadiene CH2=CH-CH=CH2 + 2 HCN → NC(CH2)4CN ...
Adiponitrile - Production - Modern Routes
... of adiponitrile is prepared by the nickel-catalysed hydrocyanation of butadiene, as discovered at duPont ... In the final stage, these pentenenitriles are subjected to a second hydrocyanation, in an anti-Markovnikov sense, to produce adiponitrile ... that the 3-pentenenitrile, formed in the first hydrocyanation, can undergo alkene metathesis to give dicyanobutenes, which are readily hydrogenated as described above ...
Hydrocyanation - History
... Hydrocyanation was first reported by Arthur and Pratt in 1954, when they homogeneously catalyzed the hydrocyanation of linear alkenes ...