Amines carbon-nitrogen bonds, hydrogenolysis

Scheme 10.9 The hydrogenation pathway of amides to amines involving hydrogenolysis of the carbonyl carbon-nitrogen bond.

Hydrogenation of diarylamines yields dialicyclic amines, but hydrogenolysis of the carbon-nitrogen bond also occurs. Dehydrogenation of DPA yields catbazole and alkyl derivatives of DPA give acridines. Dehydrogenation with sulfur gives phenothiazines (12). 

In recent years, amines have also been synthesized by nitrogen insertion into a zirconium-carbon bond followed by hydrogenolysis [75] (Scheme 28). 

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