
%0 Journal Article
%A Leslie, DR 
%A Pantelidis, S 
%T Intramolecular Catalysis of Dialkyl &#969;-Aminoalkylphosphonate Hydrolysis
%J Australian Journal of Chemistry
%D 1994/03/01
%V 47
%N 3
%P 545-559
%K 
%R https://doi.org/10.1071/CH9940545
%U https://www.publish.csiro.au/paper/CH9940545 
%X The influence that intramolecular catalysis of hydrolysis of O-alkyl S-[2-( dialkylamino )ethyl] alkylphosphonothioates by amino groups may have on the product distribution of the reaction is investigated by study of a series of model compounds. The hydrolysis of diethyl [&#969;-( ethylamino )alkyl] phosphonates and diethyl [&#969;-( diethylamino )alkyl] phosphonates has been investigated at 75&#176;C over the pH range 8.21-11.45. Contributions to hydrolysis of the ethoxy groups by intramolecular catalysis by the amino groups have been identified for [2-(amino)ethyl]- and [3-(amino) propyl ]- phosphonates. Secondary and tertiary amino groups assist hydrolysis through general base catalysis. An additional contribution to hydrolysis of the secondary amino compounds by intramolecular nucleophilic catalysis is also observed. 
