New linear and cyclic chalcogen-containing compounds have been synthesized exploiting the reactivity of bis(trimethylsilyl)selenide with strained heterocycles. A simple and efficient procedure allowed a selective access to β-functionalized selenides, diselenides, and dithiaselenepanes under mild conditions. Antioxidant catalytic activity of these compounds was investigated in the reaction of hydrogen peroxide with dithiothreitol (DTT red ). According to this assay, some of the synthesized structures exhibited a remarkable glutathione peroxidase (GPx)-like activity.
The synthesis of sulfur‐ and selenium‐containing isosters of triacyl glycerols is herein described. Regioselective fluoride‐induced ring‐opening reaction of suitable substituted thiiranes with bis(trimethyl)silyl selenide, followed by in situ S‐ and Se‐acylation with fatty acid acyl chlorides, enables the one pot synthesis of mixed chalcogeno esters in good yield. The key step of this methodology is the functionalization of S−Si and Se−Si bonds of silyl chalcogenides, generated in situ under mild conditions. A related procedure for the synthesis of functionalized selenides, bearing two thiol ester and two ester moieties, was also developed through a fine tuning of the reaction conditions. The physico‐chemical properties of these novel fatty acid chalcogeno esters have been investigated through DSC, SAXS, WAXS, FTIR and polarized optical microscopy, and compared to those of the common triglycerides in order to highlight the effect of the replacement of oxygen with other chalcogen elements in the polar head of the lipid.
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