Guilford Techno Consultants, Inc
Staudinger Reaction
Sunday, October 15, 2023 by Guilford Techno Consultants, Inc. | Name Reactions
The Staudinger reaction, discovered by Hermann Staudinger involves the reduction of organic azides by a phosphine to yield an amine. If triphenylphosphine is used, nitrogen gas and triphenylphosphine oxide are produced as by-products:
The reaction occurs in two steps. In the first step, the azide is reacted with triphenylphosphine to produce an iminophosphorane intermediate and nitrogen gas. Subsequent reaction of the iminophosphorane with water yields the desired amine product and triphenylphosphine oxide.
The Staudinger reaction is similar to the Wittig reaction in which an aldehyde or ketone is converted to an alkene through reaction with a phosphorous ylide:
Phosphorous ylides, also known as Wittig reagents, are resonance stabilized carbanions:
The mechanism for the Staudinger reaction, along with practice problems, can be found in the following presentation.
