SYSTEMES DE STRECKER ET APPARENTES - XI FORMATION ET STABILITE DE L'α-CARBOXYAMINONITRILE. INTERMEDIAIRE ESSENTIEL DANS LA SYNTHESE DES HYDANTOINES SELON BUCHERER-BERGS

Article abstract of DOI:10.1016/0040-4020(80)80137-2

The determination of the structure of the intermediate in the Bucherer-Bergs reaction (the transformation in aqueous solution of an aldehyde into the corresponding amino-acid via the hydantoin) showed that this reaction involved the formation of α-aminonitrile carbamate.The slow formation of the carbonic anhydride from the carbonate buffer limited the formation of that main intermediate which was in equilibrium with the α-aminonitrile.The variation of the stability of the carbamate vs pH is mainly determined by the concentration of CO2 dissolved in the mixture, but also by the equilibrated formation of products formed by the degradation of α-aminonitrile, i.e. the aminodinitrile and the cyanohydrin.