Synthesis and oxidation of sulfides containing an isocyanurate fragment

Abstract

The reaction of 1 (ω haloalkyl) 3,5 dimethylisocyanurates with sodium salt of methyl thioglycolate afforded the corresponding 1 [ω (methoxycarbonylmethylthio)alkyl] 3,5 dime thylisocyanurates, the oxidation of which with the system 34% aqueous H 2 O 2 -0.2 M NaHCO 3 -Mn II leads to the corresponding sulfones. The oxidation of these compounds with 34% aq. H 2 O 2 in Ac 2 O gives alternative products, viz., sulfones, sulfoxides, or α acyloxy sul fides, depending on the temperature and number of methylene groups between the isocyanurate fragment and the sulfur atom.

On the transfer of theoretical multipole parameters for restoring static electron density and revealing and treating atomic anharmonic motion. Features of chemical bonding in crystals of an isocyanuric acid derivative

“…The preparation of the starting sulfide, 1-{2-[2-(methoxycarbonylmethylthio)ethoxy]ethyl}-3,5-dimethylisocyanurate, was described previously (Shulaeva et al, 2012). The desired sulfone, 1-{2-[2-(methoxycarbonylmethylsulfonyl)ethoxy]-ethyl}-3,5-dimethylisocyanurate, was synthesized by the oxidation of the corresponding sulfide in acetonitrile using the H 2 O 2 /NaHCO 3 /MnSO 4 system (Saifina et al, 2008). A solution of aqueous H 2 O 2 (0.05 mol of H 2 O 2 as 4.4 ml of 34% solution) and aqueous NaHCO 3 (42.5 ml, 0.2 M solution) was dropwise added to the corresponding sulfide (3.33 g, 0.01 mol) in acetonitrile (50 ml), which was mixed beforehand with a catalytic amount of MnSO 4 Á7H 2 O (0.024 g, 10 À4 mol), under stirring at 20 C. The reaction mixture was further stirred for about 30 min at room temperature.…”