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

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 center dot 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 center dot 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, H-1 NMR, C-13 NMR spectroscopy and elemental analyses data.