Influence of alkali and alkaline earth ions on the O-alkylation of the lower rim phenolic-OH groups of p-tert -butyl-calix[4]arene to result in amide-pendants: Template action of K+ and the structure of K+ bound tetra-amide derivative crystallized with a p-tert -butyl-calix[4]arene anion

Amjad Ali (1) , Chebrolu P. Rao (1) , Philippe Guionneau (2)

1 Bioinorganic Laboratory, Department of Chemistry
2 ICMCB - Institut de Chimie de la Matière Condensée de Bordeaux

Role of alkali and alkaline earth ions on the formation of calix[4]arene-amide derivatives through O-alkylation of the lower rim phenolic-OH groups in general and template action of K+ in particular have been explored. Na+ and K+ ions among alkali, and Ca2+ and Sr2+ ions among alkaline earth have shown tetra-amide derivatives bound to metal ion species. Among all these, potassium salts act as template and yields a K+ bound tetra-amide derivative where the charge is counter balanced by a calix[4] arene-monoanion and the product is crystallographically characterized. Change in the amide precursor used in these O-alkylation reactions has no effect on the type of the amide derivative formed. Also demonstrated is a direct one-step reaction for the preparation of 1,3-di-amide derivative in high yield and low reaction period using CsHCO3.

Mots clés: O-alkylation at the lower rim of calix[4]arene; Template action of K+; Mono-anion of p-tert-butyl-calix[4]arene; Alkali and alkaline earth ions

Domaines: Matériaux

Amjad Ali, Chebrolu P. Rao, Philippe Guionneau. Influence of alkali and alkaline earth ions on the O-alkylation of the lower rim phenolic-OH groups of p-tert -butyl-calix[4]arene to result in amide-pendants: Template action of K+ and the structure of K+ bound tetra-amide derivative crystallized with a p-tert -butyl-calix[4]arene anion. Journal of Chemical Sciences, 2008, 120 (2), pp.237-247. ⟨10.1007/s12039-008-0029-9⟩. ⟨hal-00277240⟩