Abstract
The reaction of 2-benzylpyridine, 2- and 4-picoline N-oxides with acetic anhydride has been investigated by means of kinetic and 18O-tracer experiments. The large kinetic isotope effects found for all these reactions suggest the proton-removal step to be rate-determining. The uneven distribution of 18O between the alcohol and carbonyl O- atoms of the esters formed appears to result from the confonnational preference of the “anhydrobase” intermediates. The slight effect of salts and substituents on the rate are also discussed.
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