Tetrahedron letters

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

J Eckert, TM Chan, RM Osterman, JB Lambert, D Gala

Index: Eckert, Jeffrey; Chan, Tze-Ming; Osterman, Rebecca M.; Lambert, Joseph B.; Gala, Dinesh Tetrahedron Letters, 1999 , vol. 40, # 31 p. 5661 - 5665

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Citation Number: 7

Abstract

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.