Calix[4]arenes 3, 4 containing one or two dialkoxyphosphonylmethylol groups at the macrocycle upper rim were synthesized by reaction of 5-formyl- or 5,17-diformyl-25,27-dipropoxycalix[4]arcnes 1, 2 with trialkylphosphites in presence of dry hydrogen chloride with high yields. Formylcalixarenes 1, 2 were transformed into monoimino and diimino derivatives 5, 6 by condensation with para-toluidine. Calixarenes 7, 8 functionalized by diethoxyphosphonyl-N-paratolylaminomethyl groups were obtained by sodium-catalyzed addition of diethylphosphite to carbon-nitrogen double bonds of compounds 5, 6. Using NMR, IR spectroscopy and FAB mass spectra it was established that bis(dialkoxyphosphonylmethylol)calix [4]arenes 4 are able to dimerize because of the formation of four strong intermolecular hydrogen bonds CH-OH ... O=P at the macrocycle upper rim.
Calix[4]arenes 3, 4 containing one or two dialkoxyphosphonylmethylol groups at the macrocycle upper rim were synthesized by reaction of 5-formyl- or 5,17-diformyl-25,27-dipropoxycalix[4]arcnes 1, 2 with trialkylphosphites in presence of dry hydrogen chloride with high yields. Formylcalixarenes 1, 2 were transformed into monoimino and diimino derivatives 5, 6 by condensation with para-toluidine. Calixarenes 7, 8 functionalized by diethoxyphosphonyl-N-paratolylaminomethyl groups were obtained by sodium-catalyzed addition of diethylphosphite to carbon-nitrogen double bonds of compounds 5, 6. Using NMR, IR spectroscopy and FAB mass spectra it was established that bis(dialkoxyphosphonylmethylol)calix [4]arenes 4 are able to dimerize because of the formation of four strong intermolecular hydrogen bonds CH-OH ... O=P at the macrocycle upper rim.
Upper rim alpha-hydroxy of alpha-amino phosphonic acid derivatives of calix[4]arenes
FAILLA, Salvatore;CONSIGLIO, GIUSEPPE;
1998-01-01
Abstract
Calix[4]arenes 3, 4 containing one or two dialkoxyphosphonylmethylol groups at the macrocycle upper rim were synthesized by reaction of 5-formyl- or 5,17-diformyl-25,27-dipropoxycalix[4]arcnes 1, 2 with trialkylphosphites in presence of dry hydrogen chloride with high yields. Formylcalixarenes 1, 2 were transformed into monoimino and diimino derivatives 5, 6 by condensation with para-toluidine. Calixarenes 7, 8 functionalized by diethoxyphosphonyl-N-paratolylaminomethyl groups were obtained by sodium-catalyzed addition of diethylphosphite to carbon-nitrogen double bonds of compounds 5, 6. Using NMR, IR spectroscopy and FAB mass spectra it was established that bis(dialkoxyphosphonylmethylol)calix [4]arenes 4 are able to dimerize because of the formation of four strong intermolecular hydrogen bonds CH-OH ... O=P at the macrocycle upper rim.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
