Also known as: Staudinger reduction
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. 3-Hydroxycyclobutan-1-one web Formula of 1-(2-Fluoroethyl)azetidin-3-amine 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
References:
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Staudinger, H.; Meyer, J. Helv. Chim. Acta 1919, 2, 635–646.
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