SYNTHESIS, CONFORMATIONAL STUDIES, AND INCLUSION PROPERTIES OF [(2-PYRIDYLMETHYL)OXY]HEXAHOMOTRIOXACALIX[3]ARENES

O-Alkylation of the flexible macrocycle 1 with 2-(chloromethyl)pyridin e in the presence of Cs2CO3 resulted in the preferential formation of partial-cone-2. The cone-to-partial-cone ratio of 2 increased in the p resence of K2O3 and led to almost equal in the presence of NaH. The te mplate effect of the alkali metal cations plays an important role in t his O-alkylation reaction. The structural characterization of these pr oducts is also discussed. The two-phase solvent extraction data indica ted that tris[(2-pyridylmethyl)oxy] hexahomotrioxacalix [3]arenes 2 sh ow moderate extractability for n-butylammonium ion and high extractabi lity for Ag+. The H-1 NMR titration of cone-2 with AgSO3CF3 clearly de monstrates that a 1:1 complex is formed, which is stable on the NMR ti me scale. Thus, the synergism of cyclophane moiety and two or three lo wer-rim side chains with pyridyl groups play a significant role on the complexation of tris[(2-pyridylmethyl)oxy] derivatives cone-2 and par tial-cone-2 with Ag+ ion and n-butylammonium ion.