Tetrahedron p. 3797 - 3802 (1994)
Update date:2022-08-16
Topics:
Cerichelli, Giorgio
Mancini, Giovanna
Luchetti, Luciana
We report the bromination of some N,N-disubstituted anilines (N-ethyl-N-methylaniline, N,N-diethylaniline, N-butyl-N-methylaniline, 1-phenylpyrrolidine, 1-phenylpiperidine) both in aqueous suspension of cetyltrimethylammonium tribromide (CTAB3) and in homogeneous solution (CHCl3).In the presence of surfactant we observed a regioselectivity different from that observed in homogeneous conditions.The regioselectivity seems to depend on the nature of the substituents on the nitrogen of the aniline as well as on the temperature.An explanation based on specific interactions between the aniline and the packed structure of the aggregate is proposed.
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