Synthesis of (E)-chlorovinyl methylsulfanes via chlorothiomethylation of alkynes with HCl and dimethyl sulfoxide (DMSO) under metal-free and oxidant-free conditions has been reported. This methodology is rare, in which chlorovinyl methylsulfanes are constructed using chlorosulfanes rather than the combination of HCl and DMSO to react with alkynes. This procedure introduces a new application of DMSO, which is employed as a source of the SMe group to directly insert into the carbon-carbon triple bond of alkynes. Additionally, the reaction shows a broad substrate scope, good functional group compatibility, and excellent regioselectivity. Scheme 2. Scope of the substrates (All reactions are carried out on a 1.0 mmol scale, DMSO 1.0 mL, and all the listed yields are isolated yield) Scheme 3. A rational mechanism.
A novel environmental friendly plasticizer (TPE) derived from tung oil fatty acid with long fatty acid chain and high degree of branching was synthesized. Chemical structure of the obtained TPE was characterized with Fourier transform infrared spectroscopy (FT-IR) and 1 H NMR. TPE was used to prepare plasticized PVC blends as main plasticizer. Thermal stability, mechanical properties and migration resistance of poly (vinyl chloride) plasticized with TPE were investigated. The results showed that torque data of plasticized PVC blends reached 12.4 N·m when the mass of the TPE was 50 wt.%. TPE improved the thermal stability of PVC blends obviously than dioctyl phthalate (DOP). The leaching tests showed that PVC plasticized with TPE were with higher migration resistance than that of DOP. The excellent thermal stability and high migration resistance of PVC blends showed high application value for TPE.
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