Study of the rearrangement of N-alkylanilines to P-aminoalkylbencene. III. N-n-propil-l-14C aniline

The rearrangement of N-n-propyl aniline to p-amino propylbenzene has been studied at 250 degree centigrade using several catalysts: CoCl2, ZnCl2 and HBr. N-propyl-1-14C-aniline has been synthesized from sodium propionate-1-14C through conversion to n-propyl-1-14C-iodide and further reaction with aniline. After the rearrangement and among the reaction products both p-aminopropylbenzene and p-aminoisopropylbencene were found. To determine the 14C position in both the starting aniline and reaction products two degradation schemes are followed. In the light of experimental evidence a mechanism is set forth based on the assumption of an organic cation as intermediate. (Author) 13 refs