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Published: Kem. Ind. 56 (3) (2007) 145–150
Paper reference number: KUI-05/2007
Paper type: Conference paper
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Adamantane, the Building Block in the Construction of Macrocyclic Systems

K. Mlinarić-Majerski and I. Vujasinović


Part of our investigation was directed to the synthesis of novel macrocyclic polyethers, which contain polycyclic cage molecule, incorporated into the macrocyclic framework or attached as a side chain. We have prepared a series of adamantane-functionalized oxa-, aza- and thia-crown ethers, and studied their complexation abilities by alkali or transition metal picrate extraction experiments or by electrospray ionization mass spectrometry. In the homogeneous methanol/chloroform solutions as well as, in the extractions of metals from aqueous solution by macrocycles in chloroform, it was found that the type of heteroatom (O, N, S) and presence the adamantanesubstituents, influence the metal selectivity as well as the overall lipophilicity of the macrocyclic ligand.

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adamantane crown ethers, aza-crown ethers, crown thiaethers, polythialactones