Schmidt reaction



The Schmidt reaction is an isocyanate intermediate:

and amides:

A 2-quinuclidone.

Reaction mechanism

The carboxylic acid Schmidt reaction starts with acylium ion 1 obtained from protonation and loss of water. Reaction with amine.

The reaction is related to the Curtius rearrangement except that in this reaction the azide is protonated and hence with different intermediates.

In the amide.

Reactions involving alkyl azides

The scope of this reaction has been extended to reactions of carbonyls with alkyl β-azido-ethanol:

Variations involving lactams [5]:

References

  1. ^ Named Organic Reactions, 2nd Edition, Thomas Laue and Andreas Plagens, John Wiley & Sons: Chichester, England, New York, 2005. 320 pp. ISBN 0-470-01041-X
  2. ^ Schmidt, R.F. Ber., 1924, 57, 704.
  3. ^ The Acid-catalyzed Reaction of Alkyl Azides upon Carbonyl Compounds J. H. Boyer and J. Hamer J. Am. Chem. Soc.; 1955; 77(4) pp 951 - 954; doi:10.1021/ja01609a045 10.1021/ja01609a045
  4. ^ Intramolecular Schmidt reaction of alkyl azides Jeffrey Aube and Gregory L. Milligan J. Am. Chem. Soc.; 1991; 113(23) pp 8965 - 8966; doi:10.1021/ja00023a065
  5. ^ Cation-pi Control of Regiochemistry of Intramolecular Schmidt Reactions en Route to Bridged Bicyclic Lactams Lei Yao and Jeffrey Aubé J. Am. Chem. Soc.; 2007; 129(10) pp 2766 - 2767; (Communication) doi:10.1021/ja068919r

See also
 
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