The kinetics and mechanism of acid-catalysed chlorination by N-chlorocompounds

Abstract

Considerable attention has "been focussed on the acid-catalysed rearrangement of N-chloroacetanilide where there is specific catalysis by hydrochloric acid. Up to 1909 the rearrangement was regarded as being intramolecular (occurring by exchange of valence bonds within a single molecule). In that year this view was disputed by Orton and Jones K. J. P. Orton and W. J. Jones, Proc. Chem. Soc., 1909, 25, 196, 233, 305; J. Chem. Soc., 1909, 95, 1456; Rep. Brit. Assoc., 1910, 85; ibid., 1911, 94; 1912, 116; 1913, 136; 1914, 105; 1915, 82; K. J. P. Orton and H. King, J. Che. Soc., 1911, 99, 1185., who considered that the reaction proceeded through a reversible reaction of N-chloroacetanilide with hydrochloric acid, yielding acetanilide and chlorine, the o-and p-chloroacetanilides then being formed by attack of the chlorine on the acetanilide.