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Issue 12, 1986

Synthesis and selectivity for lithium of lipophilic 14-crown-4 derivatives bearing bulky substituents or an additional binding site in the side arm

Abstract

Two types of 6,6-disubstituted 14-crown-4 (1,4,8,11-tetraoxacyclotetradecane) derivatives have been synthesized in the hope of improving on the selectivity of the parent macrocycle for Li+, especially against Na+ and K+. Selectivity enhancement was expected to result from incorporation of bulky substituents which suppress the formation of stable sandwich-type complexes with Na+ and K+, and from the attachment of an additional binding site possessing affinity for Li+. Studies of the electrochemical selectivity of membranes containing the crown ethers showed that selectivities for Li+ with respect to Na+ and K+ are augmented in 6,6-dibenzyl- and 6-diethylcarbamoylmethyl-6-dodecyl-14-crown-4, (6) and (18), as compared with the 6-dodecyl-6-methyl derivative (2).

Article information


J. Chem. Soc., Perkin Trans. 2, 1986, 1945-1951
Article type
Paper

Synthesis and selectivity for lithium of lipophilic 14-crown-4 derivatives bearing bulky substituents or an additional binding site in the side arm

K. Kimura, H. Yano, S. Kitazawa and T. Shono, J. Chem. Soc., Perkin Trans. 2, 1986, 1945 DOI: 10.1039/P29860001945

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