Collect. Czech. Chem. Commun. 1986, 51, 677-683

Solvolysis kinetics of ethyl 3-ethoxy-3-iminopropanoate

Jaromír Kaválek, Josef Panchartek, Tomáš Potěšil and Vojeslav Štěrba

Department of Organic Chemistry, Institute of Chemical Technology, 532 10 Pardubice


Kinetics have been studied of hydrolysis and methanolysis of ethyl 3-ethoxy-3-iminopropanoate. The methanolysis rate constant is lower than the hydrolysis rate constant by about 3 orders of magnitude. The rate-limiting step of the hydrolysis consists in the nucleophilic attack of the protonated substrate by a water molecule, whereas that of the methanolysis consists in the decomposition of tetrahedral intermediate which is several orders of magnitude slower than the decomposition of the intermediate formed in the hydrolysis.