Cyanoethylation is a process for the attachment of CH2CH2CN group to another organic substrate. The method is used in the synthesis of organic compounds.[1]
Cyanoethylation entails addition of protic nucleophiles to acrylonitrile. Typical protic nucleophiles are alcohols, thiols, and amines. 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. Acrylonitrile is a Michael acceptor.[2] The reaction is normally catalyzed by a base.[3]
Cyanethylation is used to prepared numerous commercial chemicals. Detailed laboratory procedures are available for several variants of this reaction.
An alternative method for cyanoethylation entails alkylation of the substrate with 3-chloropropionitrile.
Cyanoethyl is a protecting group. It is removed by treatment with base:
This methodology is popular in the synthesis of oligonucleotides.[10]
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