Sequential mono-N-arylation of piperazine nitrogens. Part 2: The role of hydrogen bonding

Authors
Eckert, J Chan, TM Osterman, RM Lambert, JB Gala, D
Citation
J. Eckert et al., Sequential mono-N-arylation of piperazine nitrogens. Part 2: The role of hydrogen bonding, TETRAHEDR L, 40(31), 1999, pp. 5661-5665
Citations number
9
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
40
Issue
31
Year of publication
1999
Pages
5661 - 5665
Database
ISI
SICI code
0040-4039(19990730)40:31<5661:SMOPNP>2.0.ZU;2-#
Abstract
A mechanistic study of the simple sequential N-arylation of piperazine sugg ests that in an electron-withdrawing group (EWG) containing N-arylated pipe razines, hydrogen bonding of the secondary amine hydrogen is important for its non-metal catalyzed conversion to N,N'-diaryl piperazines. A combinatio n of synthetic experiments, molecular modeling, and NMR studies were carrie d out to test this hypothesis. (C) 1999 Elsevier Science Ltd. All rights re served.