The kinetics and the mechanism of the reaction of 2-chloro-4,6-dialkylamino-1,3,5-triazines with ozone

Eight 2-chloro-4,6-dialkylamino-1,3,5-triazines were reacted with ozone at pH 3. Alkyl groups were methyl, ethyl, n-propyl, i-propyl, n-butyl, t-butyl, hydrogen. Oxidative N-dealkylation and alpha-oxygenation to give an amide were obtained. Kinetic measurements were used to obtain second order rate constants and activation parameters. The entropy of activation and some semi empirical calculations suggests a mechanism occurring via addition to nitrogen concerted with hydrogen transfer. The alpha-oxygenation reaction is the metal-free oxidation of value in a green chemistry perspective.