Fragmentation of activated n,n-dibenzyl-3-phenylalanine derivatives

Summary Like the hydrochlorides, some other activated derivatives of dibenzylamino acids are capable of undergoing the fragmentation reaction, though under more severe conditions, as would be expected for the mechanism proposed [1]. However, the reaction is more complex than the suggested mechanism would indicate, and it was therefore necessary to introduce the further assumption of two protonized forms of dibenzylamino acid derivatives activated at the carboxyl. Fragmentation is catalyzed by acids and inhibited by substances capable of acting as proton acceptors (diethylaniline, tetrahydrofuran, dioxane).The author expresses his thanks to A. F. Sholin for carrying out the Chromatographie analysis.