Acidity and N-methylation of N-aryl-N '-cyanoguanidines

Authors
Cunningham, ID Cox, BG Wan, NC Povey, DC Smith, GW
Citation
Id. Cunningham et al., Acidity and N-methylation of N-aryl-N '-cyanoguanidines, J CHEM S P2, (4), 1999, pp. 693-697
Citations number
20
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
ISSN journal
03009580 → ACNP
Issue
4
Year of publication
1999
Pages
693 - 697
Database
ISI
SICI code
0300-9580(199904):4<693:AANON'>2.0.ZU;2-M
Abstract
Acid dissociation constants in water have been determined for proton loss f rom a series of N-aryl-N'-cyanoguanidines 1. Treatment,of the same compound s with a strong base, butyllithium, followed by excess methyl iodide leads to successive N-methylation to yield mono-, di- and tri-methylated N-aryl-N ' -cyanoguanidines, The mechanism of the methylation is discussed.