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Staudinger reaction
The Staudinger reaction or Staudinger reduction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane intermediate. Combined with the hydrolysis of the aza-ylide to produce a phosphine oxide and an amine, this reaction is a mild method of reducing an azide to an amine. Triphenylphosphine is commonly used as the reducing agent, yielding triphenylphosphine oxide as the side product in addition to the amine.
The reaction was discovered by and named after Hermann Staudinger.
An example of a Staudinger reduction is the organic synthesis of this pinwheel compound:
:
==Reaction mechanism==
The reaction mechanism centers around the formation of an iminophosphorane through nucleophilic addition of the phosphine at the terminal nitrogen atom of the azide and expulsion of nitrogen. This intermediate is then hydrolyzed in the second step to the amine and triphenylphosphine oxide
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