Staudinger reaction

The Staudinger reaction is a chemical reaction, which is used in the synthesis of primary amines of azides. It is named after its developer Hermann Staudinger.

The Staudinger reaction is an alternative to other mild amine syntheses. The azides required are usually easily accessible by substitution of the corresponding haloalkanes.

Reaction mechanism

The Staudinger reaction begins with the nucleophilic attack of triphenylphosphine on used azide. The resulting cyclized phosphazide now to a four-membered ring structure, which reacts with the elimination of molecular nitrogen at a phosphazene. By aqueous workup, the phosphazene is converted to an amine and triphenylphosphine oxide removed.

Staudinger ligation

A discovered in 2000, further development of peptide and protein ligation is known as the Staudinger ligation.

Criticism

The atom economy of the Staudinger reaction is poor because obtained in the synthesis, stoichiometric amounts of triphenylphosphine oxide. Therefore, the reaction is mainly as laboratory procedures and less as a technical process of interest.