Staudinger reaction

For the reaction between imines and ketenes to form β-lactams, see Staudinger synthesis.
Staudinger reaction
Named after Hermann Staudinger
Reaction type Organic redox reaction
Identifiers
Organic Chemistry Portal staudinger-reaction
RSC ontology ID RXNO:0000066

The Staudinger reaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane.[1][2] The reaction was discovered by and named after Hermann Staudinger.[3] The reaction follows this stoichiometry:

R3P + R'N3 → R3P=NR' + N2
  1. ^ Gololobov, Y. G. (1981), "Sixty Years of Staudinger Reaction", Tetrahedron, 37 (3): 437–472, doi:10.1016/S0040-4020(01)92417-2
  2. ^ Gololobov, Y. G.; Kasukhin, L. F. (1992), "Recent Advances in the Staudinger Reaction", Tetrahedron, 48 (8): 1353–1406, doi:10.1016/S0040-4020(01)92229-X
  3. ^ Staudinger, H.; Meyer, J. (1919), "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine", Helv. Chim. Acta, 2 (1): 635, doi:10.1002/hlca.19190020164