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
^Gololobov, Y. G. (1981), "Sixty Years of Staudinger Reaction", Tetrahedron, 37 (3): 437–472, doi:10.1016/S0040-4020(01)92417-2
^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
^Staudinger, H.; Meyer, J. (1919), "Über neue organische Phosphorverbindungen III. Phosphinmethylenderivate und Phosphinimine", Helv. Chim. Acta, 2 (1): 635, doi:10.1002/hlca.19190020164
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The Staudingerreaction is a chemical reaction of an organic azide with a phosphine or phosphite produces an iminophosphorane. The reaction was discovered...
He is also known for his discovery of ketenes and of the Staudingerreaction. Staudinger, together with Leopold Ružička, also elucidated the molecular...
behavior. The Staudinger ligation is a reaction developed by the Bertozzi group in 2000 that is based on the classic Staudingerreaction of azides with...
reaction carries particular importance in the synthesis of β-lactam antibiotics. The Staudinger synthesis should not be confused with the Staudinger reaction...
in bioconjugation chemistry. Some important reactions are modification of ketone and aldehydes, Staudinger ligation with organic azides, copper-catalyzed...
react with PPh3 to give phosphanimines, analogues of OPPh3, via the Staudingerreaction. Illustrative is the preparation of triphenylphosphine phenylimide:...
their participation in the "click reaction" between an azide and an alkyne and in Staudinger ligation. These two reactions are generally quite reliable, lending...
who competed from 1978 to 1989 Staudinger synthesis, method to prepare β-lactams Staudingerreaction, chemical reaction in which the combination of an...
RNH2 → Ph3PNR + 2 RNH3+Br− The method is used when the conventional Staudingerreaction is not applicable, i.e. when the organic azide is not available to...
example shows the synthesis of a β-lactam by the reaction of a ketene with an imine (see Staudinger synthesis): Ketenes are generally very reactive, and...
hydride or a tertiary phosphine, such as triphenylphosphine in the Staudingerreaction, with Raney nickel or with hydrogen sulfide in pyridine. Oseltamivir...
step the alcohol is oxidized in a Swern oxidation to ketone 11. A Staudingerreaction with triphenylphosphine closes the ring between the ketone and the...
of phosphine ligands with trimethylsilyl azide, also known as the Staudingerreaction: PR3 + Me3SiN3 → Me3SiN=PR3 + N2 Starting from these silyl compounds...
studied reactions in this field are the 4π Staudinger β-lactam synthesis and the 4π Nazarov reaction; asymmetric catalysis of both reactions have been...
Regitz et al. in 1994. However, in the presence of excess azide, the Staudingerreaction can take place, which transforms the yellow λ3σ3 1H-2-iminophosphete...
3-sulfolene forms in a 1,3-dipolar cycloadduct: In 1935, H. Staudinger and co-workers found that the reaction of butadiene and SO2 at room temperature gives a second...
formula R3P=NSiMe3 are particularly useful. They are prepared by the Staudingerreaction of tertiary phosphines with trimethylsilyl azide: R3P + N3SiMe3 →...
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