ChemInform Abstract: Sequential Mono-N-arylation of Piperazine Nitrogens. Part 2. The Role of Hydrogen Bonding.

A mechanistic study of the simple sequential N-arylation of piperazine suggests that in an electron-withdrawing group (EWG) containing N-arylated piperazines, hydrogen bonding of the secondary amine hydrogen is important for its non-metal catalyzed conversion to N,N'-diaryl piperazines. A combination of synthetic experiments, molecular modeling, and NMR studies were carried out to test this hypothesis. (C) 1999 Elsevier Science Ltd. All rights reserved.