Synthesis of N-(4'-Benzo[15-crown-5])thiophenoxyphenylaminoglyoxime and its complexes with some transition metals

Abstract

4-(Chloroacetyl)diphenyl thioether (1) was synthesized from chloroacetyl chloride and diphenyl thioether in the presence of AlCl3 as catalyst in a Friedel-Crafts reaction. Subsequently, its keto oxime (2) and glyoxime (3) derivatives were prepared. N-(4'-Benzo[15-crown-5] thiophenoxyphenylaminoglyoxime (H2L) and its sodium chloride complex (H2L • NaCl) were prepared from 4-(thiophenoxy) chlorophenylglyoxime (3), 4'-aminobenzo[15-crown-5] and sodium bicarbonate or sodium bicarbonate and sodium chloride. Ni(II), Co(II) and Cu(II) complexes of H2L and H2L • NaCl have a metal-ligand ratio of 1:2 and the ligand coordinates through the two N atoms, as do most of the vic-dioximes. The BF2-capped Ni(II) mononuclear complex of the vic-dioxime was prepared. The macrocyclic ligands and their transition metal complexes were characterized on the basis of FT-IR, 1H NMR, 13C NMR spectroscopy and elemental analyses data. © 2007 Springer Science+Business Media B.V.