La migration de groupes carboxamides lors de la transposition benzilique d'amides α,β‐dicarbonylés. 24e Communication sur les réductones et les composés tricarbonylés‐1,2,3 [1]

Under the conditions of the benzilic acid rearrangement, α,β-diketobutyryl-di-phenylamide (Ia) and -N-methylanilide (Ib) are transformed into tartronic acid derivatives (VI), which decarboxylate to lactamides VII. It is proved by 14-labelling of Ia, that the reaction takes place by carbonamide group migration. The reaction was followed kinetically by polarography at a fixed potential; at low pH the velocity is proportional to [OH⊖], at higher pH it becomes independent of [OH⊖], which is explained by complete transformation of I into its hydrate-anion. The equilibrium between I and its hydrate was measured by UV.-spectroscopy.