Kinetics,catalysis, and mechanism of isomerization of N-[(benzotriazol-1-yl)methyl]anilines into the benzotriazol-2-yl derivatives |
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Authors: | Alan R Katritzky Stanislaw Rachwal Bogumila Rachwal John W Frankenfeld |
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Abstract: | 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°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 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. © 1995 John Wiley & Sons, Inc. |
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