Cyanoethylation

Cyanoethylation is a process for the attachment of CH2CH2CN group to another organic substrate.

[1] Cyanoethylation entails addition of protic nucleophiles to acrylonitrile.

Two new bonds form: C-H and C-X (X = carbon, nitrogen, sulfur, phosphorus, etc): The β-carbon atom that is furthest from the nitrile group is positively polarized and therefore binds the heteroatom on the nucleophile.

An alternative method for cyanoethylation entails alkylation of the substrate with 3-chloropropionitrile.

It is removed by treatment with base: This methodology is popular in the synthesis of oligonucleotides.