1,3,5-Trialkyl-hexahydro-1,3,5-triazines–N-methylenealkylamines equilibria. 1H NMR studies in solutions

The behavior of 1,3,5-trialkyl-1,3,5-hexahydrotriazines (A) in a variety of solvents was investigated by 1H NMR. A are stable for linear alkyls in deuterated solvents such as chloroform, benzene, acetone, dioxane, dimethylsulfoxide and acetonitrile. In case of branched alkyls, A are in equilibrium with N-methylenealkylamines (B). The A/B ratio depends on solvent, concentration of the sample and temperature. A react easily with methanol and lead to the formation of N-(methoxymethyl)amines (C), which are in equilibrium with B. Both the quantitative evaluation of A–B equilibrium in solutions as well as the formation of C in methanol was described for the first time.