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.