Molecular rearrangements. Part IX. The acid-catalysed rearrangement of N-chloroacetanilide

Abstract

The rearrangement of N-chloroacetanilide in 99% acetic acid is compared with that of the N-chloro-derivatives of α-chloroacetanilide and of α-fluoroacetanilide, toluene-p-sulphonic acid or hydrochloric acid being used as promoters.

With toluene-p-sulphonic acid, N-chloroacetanilide rearranges the fastest and N-chloro-α-fluoroacetanilide the slowest.

The rate of change with hydrochloric acid is in the reverse order: PhNCl·CO·CH₂F > PhNCl·CO·CHCl > PhNCl·CO·CH₃. These observations are discussed.