Nachbargruppeneffekte bei der Aminolyse von Estern, II Die Aminolyse von 2-(2-Hydroxybenzyl)phenylacetaten / Neighboring Group Effects in the Aminolysis of Esters, II The Aminolysis of 2-(2-Hydroxybenzyl)phenylacetates

Abstract

<jats:title>Abstract</jats:title><jats:p> The aminolysis of 2-(2-hydroxybenzyl)phenyl acetates with n-butylamine in dioxane is much faster than for the corresponding 2-(2-methoxybenzyl)phenyl acetates or 2-methyl-phenyl acetates. The kinetic results can be explained by two equivalent mechanisms. Both of them include the formation of a 1:1-complex between 2-(2-hydroxybenzyl)phenyl acetate and n-butylamine which is formed in an equilibrium. The reaction of this complex according to a second order rate law seems to be more probable than the reaction of the free ester according to a third order rate law.</jats:p>