Journal of Organic Chemistry p. 5105 - 5110 (1989)
Update date:2022-08-03
Topics:
Newkome, George R.
Kiefer, Garry E.
Kohli, Dalip K.
Xia, Yuan-Jiao
Fronczek, Frank R.
Baker, Gregory R.
The synthesis of crown ether derivatives containing the dipyridino subunit is described.Direct nucleophilic displacement by the glycolates of di-, tri-, tetra-, penta-, and hexaethylene glycol on 6,6'-bis(chloromethyl)-2,2'-dipyridine resulted in an extensive series of macrocycles; the addition of Co(II), Cu(II), Zn(II), and Pd(II) salts to the 1:1- and 2:2-macrocycles generated the corresponding complexes.X-ray crystallography confirmed the structure of the 2:2-macrocycle derived from diethylene glycol as well as the related unsymmetrical derivative arising from glycol fragmentation.The ligands were fully characterized by 1H NMR spectroscopy, and a europium shift study was conducted on a representative 1:1-macrocycle in order to establish the preferred site of complexation.
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