A New Synthesis Of Thiosulfonates And Deuterated Thiosulfonates And Diols

A new synthesis of thiosulfonates and deutearated thiosulfonates and free-metalcatalytic oxidation of olefin to1,2-diol are reported in this dissertation.A new synthesis of thiosulfonates starting from thiophenols and cyanuricchloride （TCT）-activated DMSO is reported in the first part of this dissertation. TCTand thiophenol react in DMSO, get thiosulfonates, although the yields of the reactionsare moderate, this method enables the incorporation of SCD3group of DMSO-d6intothiosulfonates. This is the first synthesis of deuterated thiosulfonates with a labellingpurity above99%. Furthermore, a plausible mechanism for the reaction ofTCT-activated DMSO and thiophenols is proposed based on the experiments, andproven by trapped chloromethane gas from the reaction. In addition, the cytotoxicityof the thiosulfonates is reported for the first time.In the second part of this dissertation, a method for olefin oxidation to1,2-diolusing sulfuric acid （H2SO₄） as promoter and hydrogen peroxide as oxidant in dioxaneand water mixed solvent is reported. The yields for the products from steroids are thebest to our knowledge; the yields for the products from acyclic olefins are moderate.Plausible mechanism is proposed based on the experiments using potassiumpersulfornateIn conclusion, the new synthesis of the partially deuterated thiosulfonatesreported herenin is operationally simple, and requires inexpensive and commerciallyavailable reagents. Although the yield is moderate, this is the first method forsynthesis of deuterated thiosulfonates. Free-metal catalytic dihydroxylation of steroidswould be useful in medicinal chemistry.