Synthesis and oxidation of sulfides containing an isocyanurate fragment

The reaction of 1-(ω-haloalkyl)-3,5-dimethylisocyanurates with sodium salt of methyl thioglycolate afforded the corresponding 1-[ω-(methoxycarbonylmethylthio)alkyl]-3,5-dimethylisocyanurates, 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 sulfides, depending on the temperature and number of methylene groups between the isocyanurate fragment and the sulfur atom.