Kinetics, Catalysis, and Mechanism of Isomerization of N-anilines into the Benzotriazol-2-yl Derivatives

Article abstract of DOI:10.1002/kin.550270406

The 1H NMR technique was applied for the measurement of the isomerization rates of N-ethyl-N-<(benzotriazol-1-yl)methyl>aniline (4) and 4-butyl-N-<(benzotriazol-1-yl)methyl>aniline (7) to the corresponding benzotriazol-2-yl isomers in dioxane-d8 at 35 deg C.The rate constants obtained for pure dioxane-d8 were 1.62 and 0.28 h^-1 for 4 and 7, respectively.For both compounds, addition of acetic acid to the dioxane solutions accelerated the isomerizations whereas addition of triethylamine retarded it strongly.Addition of water slowed the isomerization of 4 but accelerated that of 7: the different effects operating in the two cases are discussed and rationalized.