Aromatic Tertiary Amines and n-Butyl Nitrite

The reaction between alkyl nitrites, particularly n-butyl nitrite, and tertiary aromatic amines under a variety of experimental conditions promptly yielded products of N-dealkylation-N-nitrosation, ring nitration, ipso-substitution and, occasionally, combinations of these processes. Aminoethers were detected as final products and intermediates on the way to N-nitrosations. Reaction pathways are suggested for some of the observed behaviours on the basis of experimental evidences whereas other alternatives are discarded.