Rearrangements of diphenylamine derivatives. Part III. The Reilly-Hickinbottom rearrangement

Abstract

N-Methyl-, N-ethyl-, and N-isopropyl-diphenylamine rearrange in the presence of cobalt(II) chloride at 340° to give the corresponding N-(4- and 2-alkylphenyl)anilines; N-n-propyldiphenylamine gives both C-n-propyl and C-isopropyl products under identical conditions. The ratios of isomers produced indicate that carbonium ions participate in the formation of the C-isopropyl products, but that bimolecular alkyl transfer is involved in the other cases.