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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]
Author(s) -
Dahn H.,
Karoui S.
Publication year - 1969
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19690520832
Subject(s) - chemistry , hydrate , medicinal chemistry , transposition (logic) , polarography , stereochemistry , organic chemistry , inorganic chemistry , philosophy , linguistics
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.