Abstract
The rearrangement of N-chloroacetanilide in 99% acetic acid is compared with that of the N-chloro-derivatives of propionanilide, butyranilide, α-chloro, α-dichloro and α-trichloroacetanilides in presence of benzoic acid, toluene- p-sulphonic acid or hydrochloric acid as promoters. The rate of change increases progressively with increasing +I effect and decreases with increasing −I effect of substituents on the acyl group. The rearrangements with different carboxylic acids and sulphonic acid catalysts are best interpreted as intermolecular chlorination, the protonated N-chloro-compounds acting as electrophilic chlorinating agents.
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