Facile synthesis of symmetric thiosulfonates by oxidation of disulfide with oxone/MX (MX = KBr, KCl, NaBr and NaCl)

Selenomethoxylation of Alkenes Promoted by Oxone®

“…Regarding its use in the synthesis of organochalcogen compounds, Oxone® was used in the oxidation of sulfides to sulfoxides and sulfones, oxidation of thiols to sulfonic acids, oxyhalogenation of thiols and disulfides, oxidative coupling of thiols to disulfides, oxidation of selenides to selenones, and in the enantioselective oxidation of disulfides . Oxone® was used to prepare symmetric thiosulfonates, 3‐arylthio indoles, and 2‐aminobenzothiazoles …”

Cu(OAc)2/I2‐Mediated Direct Sulfonylation of Benzo[d]imidazoles with Disulfides

“…Our second concern was the pathway of this sulfonylation. We reasoned that diphenyldisulfide could be oxidized to thiosulfonate ( 31) under the standard condtions, and then underwent a sulfonylation with benzoimidazole to afford the target product. To prove this hypothesis, thiosulfonate ( 31 ) was reacted with benzoimidazole, and the sulfonylation was carried out to give product ( 3 ) in 87 % yield along with a 28 % yield of disulfide ( 1 a ) (Scheme , Eq 2).…”

Thiosulfonates as Emerging Reactants: Synthesis and Applications

“…Oxone ® (potassium peroxymonosulfonate, KHSO 5 /KHSO 4 /K 2 SO 4 in a 2:1:1 molar ratio) is a commercially available, non‐toxic and highly stable oxidant (Table ). It was employed by Natarajan in 2015 for the oxidation of disulfides ( 3 ) in combination with substoichiometric MX (MX=KBr, KCl, NaBr or NaCl) in aqueous acetonitrile (Scheme , route 15) . The method has been used for the oxidation of aliphatic and aromatic disulfides ( 3 ) containing electron‐donating and electron‐withdrawing groups.…”