Further Information
Literature
Related Reactions
Appel Reaction
Delépine Reaction
Eschweiler-Clarke Reaction
Gabriel Synthesis
Mitsunobu Reaction
Staudinger Reaction
Staudinger Reduction
Azides may be converted to amines by hydrogenation, but another possibility is the Staudinger Reaction, which is a very mild azide reduction. As there are a variety of methods for preparing azides readily, the Staudinger Reaction makes it possible to use -N3 as an -NH2 synthon.
Mechanism
Triphenylphosphine reacts with the azide to generate a phosphazide, which loses N2 to form an iminophosphorane. Aqueous work up leads to the amine and the very stable phosphine oxide.
W. Q. Tian, Y. A. Wang, J. Org. Chem. 2004, 69, 4299.
DOI
F. L. Lin, H. M. Hoyt, H. v. Halbeek, R. G. Bergman, C. R. Bertozzi, J. Am.
Chem. Soc, 2005, 127, 2686.
DOI
