Thorpe-Ziegler method

What is Thorpe-Ziegler method?

The Thorpe-Ziegler method, also known as the Ziegler method, is a process for the synthesis of macrocyclic ketones by the cyclization of dinitriles in the presence of an ether-soluble metal alkylanilide and a dialkyl ether solvent. The resulting imino-nitrile is then hydrolyzed to yield the desired macrocyclic ketone. The reaction yield is influenced by the ring size of the product and is typically performed at high dilution.

Thorpe-Ziegler method - Ziegler method
Thorpe-Ziegler method

References

Ziegler, K., Eberle, H. and Ohlinger, H. (1933), Über vielgliedrige Ringsysteme. I. Die präparativ ergiebige Synthese der Polymethylenketone mit mehr als 6 Ringgliedern. [On multi-membered ring systems. I. The preparatively productive synthesis of polymethylene ketones with more than 6 ring members.] Justus Liebigs Ann. Chem., 504: 94-130. https://doi.org/10.1002/jlac.19335040109

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