Synthèses et propriétés de Schiff IV. Étude cinétique de la solvolyse d'une famille d'ɑ-phénylimino-benzoyl-acétanilides (PIBAZ)

In: Bulletin de la Classe des sciences, Band 56, Heft 1, S. 886-903

Abstract

A series of azomethines derivated from the α-phenylimino-benzoyl-acetanilide (PIBA) of general formula, PIBAZ : [formula] with [formula], was submitted to acidic solvolysis.
Experimental results of a kinetic study, in an alcohol-water solvent, led to develop a reaction scheme of two nucleophilic additions simultaneously occuring at the protonated azomethinic bond : [formula]
the first one (I) giving an amino-ether (ki) which can only reverse to the original reactants (k-1) and the second one (II) generating an amino-alcohol(kII) which rapidly decomposes into the final products (P) : α, β-dioxo-dihydrocinnamanilide (C6H5— CO— CO— CO— NH— C6H5) and the corresponding aniline (Z— C6H4— HN2). This process undergoes general acid-base catalysis.