Kinetics, catalysis, and mechanism of isomerization of N-[(benzotriazol-1-yl)methyl]anilines into the benzotriazol-2-yl derivatives

✍ Scribed by Alan R. Katritzky; Stanislaw Rachwal; Bogumila Rachwal; John W. Frankenfeld

• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 425 KB
• Volume: 27
• Category: Article
• ISSN: 0538-8066
• DOI: 10.1002/kin.550270406

✦ Synopsis

The 'H NMR technique was applied for the measurement of the isomerization rates of N-ethyl-N-[( benzotriazol-1-y1)methyllaniline (4) and 4-butyl-N-[( benzotriazol-1-y1)methylIaniline (7) to the corresponding benzotriazol-2-yl isomers in dioxane-d8 at 35°C. The rate constants obtained for pure dioxane-d8 were 1.62 and 0.28 h-l for 4 and 7, respectively. For both compounds, addition to 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.