Thorpe-Ziegler Reaction

Thorpe-Ziegler Reaction

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  • Characteristics

The reaction between a nitrile and an alkoxide base leads to the formation of a β-iminonitrile from which an α-cyanoketone is obtained by mild acid hydrolysis. This reaction is known as the Thorpe reaction when intermolecular, and the Thorpe-Ziegler reaction when intramolecular.  It is to say that this reaction is a series of Claisen condensation.

The Thorpe-Ziegler reaction is especially useful in the formation of five- to eight membered rings and for rings with more than thirteen members, although it fails for nine- to twelve-membered rings.

 

  • Literature reference

・ Baron, H.; Remfry, F. G. P.; Thorpe, Y. F. J. Chem. Soc. 190485, 1726.
・ Karl Ziegler et al. Ann. 1933504, 94.
・ Schaefer, J. P.; Bloomfield, J. J. Org. React. 196715, 1.

 

  • Reaction mechanism

Thorpe_Ziegler_2

 

  • Related Books

  • Related Links

Thorpe Reaction - Wikipedia

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