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The rate of the aminolysis of 2-(2-hydroxybenzyl)phenylacetates with n-butylamine in dioxane is diminished by the addition of triethylamine. This can be quantitatively described by the competitive formation of complexes between monoacetate and n-butylamine or triethylamine, if the assumption is made, that the complex with triethylamine is aminolysed slowly or not at all. The neighboring group effect in aminolysis cannot be explained therefore by a base catalysed decomposition of the tetrahedral intermediate.

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Nachbargruppeneffekte bei der Aminolyse von Estern, III.  Der verlangsamende Einfluß von Triethylamin bei der Aminolyse von 2-(2-Hydroxybenzyl )phenylacetaten / Neighboring Group Effects in the Aminolysis of Esters, III.  The Rate Diminishing Influence of Triethylamine in the Aminolysis of 2-(2-Hydroxybenzyl)phenylacetates