Staudinger reaction

Also known as: Staudinger reduction

Schematic of the Staudinger reaction. Reagents: organic azide, PPh3, water. Product: primary amine.

The Staudinger reaction is an organic reaction used to convert an organic azide to a primary amine using a PR3 compound (such as triphenylphosphine) and water. The mechanism begins with attack of the phos-phorus on the far nitrogen of the organic azide to give a phosphazide intermediate. This intermediate then goes through a rearrangement that releases a molecule of nitrogen gas and forms a N-P ylide. The molecule of water then attacks the phosphorus atom and a series or proton transfer steps follow to result in the formation of the final primary amine and a triphenylphosphine oxide by-product.[1]


Mechanism of the Staudinger reaction.


Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635–646.