A comparison of the reactions of some ethyl N-Arylcarbamates with those of the corresponding acetanilides. I. Nitration

Abstract

The reactions of some ethyl N- arylcarbamates and of the corresponding acetanilides towards 1 equiv. of sodium nitrate in concentrated sulfuric acid at 0-5° have been compared with one another and have been found to exhibit significant differences. Except in the case of the unsubstituted analogues, nitration of the carbamates was found to occur significantly more quickly than that of the acetanilides as shown by ( i ) a representative competitive nitration, and (ii) the fact the carbamates containing a nitro group are nitrated smoothly whereas the corresponding nitroacetanilides are slow to react. On the basis of competitive reactions, it is suggested that this difference in reactivity is due to steric factors.