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

✍ Scribed by Jeffrey Eckert; Tze-Ming Chan; Rebecca M. Osterman; Joseph B. Lambert; Dinesh Gala

Book ID
104261887
Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
259 KB
Volume
40
Category
Article
ISSN
0040-4039

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✦ Synopsis

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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✍ Jeffrey Eckert; Tze-Ming Chan; Rebecca M. Osterman; Joseph B. Lambert; Dinesh Ga πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 27 KB πŸ‘ 1 views

Sequential Mono-N-arylation of Piperazine Nitrogens. Part 2. The Role of Hydrogen Bonding. -Piperazine can be selectively monoarylated with electron deficient aryl halides. However, o-chloronitrobenzene gives a 1:1 mixture of mono-and diarylated product, a fact which is explained by the activation