| Several of hydrophilic mesocyclic trithioethers and macrocyclic hexathioethers have been synthesized. Bis(2-mercaptoethyl)sulfide and bis(3-mercaptopropyl)sulfide have been prepared and cyclized with several dihalides (1,3-dibromo-2-propanol, 1,3-dichloroacetone, bis(2-bromomethyl)-1,3-propanediol, ({dollar}pm{dollar})-1,4-dibromo-2,3-butanediol, and 3,3{dollar}spprime{dollar}-dichloropivalic acid) to make different hydrophilic monocyclic thioethers. The general procedures for the preparation of mesocyclic trithioethers and macrocyclic hexathioethers utilize cesium carbonate in dimethylformamide and sodium ethoxide in ethanol, respectively. Most of the reactions give products with yields within a 10 to 30% range. Many of these products are hydroscopic, especially the macrocycles 20S6-9,9,19,19-tetramethanol (XIII) and 9,19-dimethyl-20S6-9,19-diacid (XIV) which are deliquescent. Complexation studies upon these compounds with Cd(II), Ni(II), Fe(II) at 2:1 or 1:1 ratio have also been carried out in CH{dollar}sb3{dollar}NO{dollar}sb2{dollar}/Ac{dollar}sb2{dollar}O solution. All the ligands can form Cd(II) complexes. Most of the ten- and twenty-membered ring ligands are good for Ni(II) and Fe(II) complexation as well. |
