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First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. The intermediate, e.g. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: R 3 P=NR' + H 2 O → R 3 P=O + R'NH 2. The overall conversion is a mild method of reducing an azide to an amine.
In chemistry a phosphine imide (sometimes abbreviated to phosphinimide) also known as a iminophosphorane is a functional group with the formula R 3 P=NR. While structurally related to phosphine oxide its chemistry has more in common with phosphonium ylides .
In terms of mechanism, such reactions proceed via the nucleophilic addition giving a hemiaminal-C(OH)(NHR)- intermediate, followed by an elimination of water to yield the imine (see alkylimino-de-oxo-bisubstitution for a detailed mechanism). The equilibrium in this reaction usually favors the carbonyl compound and amine, so that azeotropic ...
The azido alcohol is then reduced with the use of a trialkylphosphine such as triphenylphosphine in a manner similar to the Staudinger reaction, concomitant with loss of N 2. The resulting phosphanimine (formerly called iminophosphorane) intermediate is then attacked by the alcohol, with oxygen forming a bond with the phosphorus atom. Forming a ...
They are prepared by the Staudinger reaction of tertiary phosphines with trimethylsilyl azide: R 3 P + N 3 SiMe 3 → R 3 P=NSiMe 3 + N 2. R 3 P=NSiMe 3 undergoes alcoholysis to give the parent imine: R 3 P=NSiMe 3 + MeOH → R 3 P=NH + MeOSiMe 3. Ammonia can be used in place of alcohol. [5] [2] Lithium phosphinimides are produced by ...
Mechanism of iminophosphorane formation Aza-ylides can be obtained via the reaction of a tertiary phosphine and an organic azide with the loss of dinitrogen. Triphenylphosphine is a commonly used phosphine.
The reaction carries particular importance in the synthesis of β-lactam antibiotics. [2] The Staudinger synthesis should not be confused with the Staudinger reaction, a phosphine or phosphite reaction used to reduce azides to amines. Reviews on the mechanism, stereochemistry, and applications of the reaction have been published. [3] [4] [5]
The first phosphinoimidate complexes were prepared by reaction of phosphines with molybdenum and tungsten nitrido complexes: MNCl 3 + PPh 3 → M(NPPh 3)Cl 3. This reaction is accompanied by reduction of the metal from +VI to +IV and phosphorus from (III) to (V). The main limitation of this reaction is the relative rarity of metal nitride ...