Direct synthesis of sulfonated azacalixarenes in water.
Successive treatment of cyanuric chloride with two aromatic diamines, at least one of them sulfonated, yields water-soluble sulfonated azacalix[4]arenes which may be isolated by crystallisation. Functionalised azacalixarenes may be made by first displacing two chloro substituents from the cyclisation precursor. Attempted formation of an azacalix[6]arene led to a dimeric species for which two structures may be proposed, one of them an azacalixarene catenane.
Clayden
Jonathan
J
School of Chemistry, University of Manchester, Oxford Road, Manchester, M13 9PL, UK. clayden@man.ac.uk
Rowbottom
Stephen J M
SJ
Ebenezer
Warren J
WJ
Hutchings
Michael G
MG
D001372:Aza Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D015394:Molecular Structure; D010636:Phenols / Q000138:chemical synthesis* / Q000737:chemistry; D014867:Water / Q000737:chemistry*
D001372:Aza Compounds; D010636:Phenols; C121325:calix(4)arene; D014867:Water; D047250:Calixarenes