The Cleavage of Non-enolizable Ketones with Sodium Amide

Hamlin, K. E.; Weston, Arthur W.


In this chapter the Haller-Bauer is defined as the action of sodium amide on a non-enolizable ketone causing cleavage of a carbon-to-carbon bond and resulting in the formation of an amide and a hydrocarbon. Textbook definitions have limited the reaction to the alkylation of ketones in which sodium amide acts a condensing agent or have considered it a combination of the alkylation and cleavage reactions. Haller and Bauer reported the isolation of benzamide after the treatment of benzophenone with sodium amide in boiling benzene or toluene and followed this observation with an extended study of the reaction. A modification of the Haller-Bauer reaction involving the use of a fused eutectic mixture of sodium an potassium amides has been applied to certain alicyclic and bicyclic terpenoid ketones as well as to some amides.