SYNTHESIS AND COMPLEX-FORMING PROPERTIES OF CROWN-ETHERS INCORPORATING GLUCURONIC-ACID MOIETIES

Crown ethers 1 and 4 of the 18-crown-6 type containing two glucose uni ts have been oxidised by KMnO4 into mono- and dicarboxylic acid deriva tives (5 and 11), and derivatives with different lipophilicities of th e above crown ethers, namely the acetyl, benzyl and butyl derivatives (8-10, 13, 14) and methyl esters (6 and 12) have been synthesized. The association constants (K-a) with Li, Na, K and NH4 cations measured i n CHCl3 indicate that complexing ability increases on introduction of carboxy groups, and selectivity changes in favour of the Na cation. Th ese compounds were able to transport alkyl-ammonium salts through a CH Cl3 liquid membrane, displaying, however, no chiral recognition abilit y.