Tetrahedron Letters p. 5661 - 5665 (1999)
Update date:2022-08-05
Topics:
Eckert, Jeffrey
Chan, Tze-Ming
Osterman, Rebecca M.
Lambert, Joseph B.
Gala, Dinesh
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.
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