107. Molecular rearrangements. Part IV. The thermal rearrangement of N-chloroacetanilide

Abstract

Evidence is presented in support of the view that the rearrangerncnt of N-chloroacetanilide in the fused state is an intermolecular chlorination.IT is known that N-chloroacetanilide changes above its melting point into a mixture of 0-and P-chloroacetanilide ; other N-chloroacylarylamides behave simi1arly.l" Therc arc already sufficient observations to exclude belief that this migration is a true intramolecular rearrangement, if the term is used in the strict sense of implying that the chlorine remains within the confines of the molecule. Thus, Bradfield5 found that at 100" N-chloroacetanilide gives, not only 0-and p-chloroacetanilide, but also some acetanilide and 2,4-dichloroacetanilide as well as unidentified material and acid fumes.