Anodic acetamidosulphenylation of alkenes via anodic oxidation of disulphides

Additions to alkenes via metal ion-promoted oxidation of 2,2′-dipyridyl disulphide and bis-(2-aminophenyl) disulphide

“…General methods are described earlier.' (8).--Copper( 11) acetate (200 mg) was dissolved in a mixture of dichloromethane (50 ml) and trifluoroacetic acid (4 ml) at room temperature. Bis-(2aminophenyl) disulphide (3) (1.6 g) and then cyclohexene (3.2 g) were added in rapid succession.…”

Electrochemical Synthesis of Organic Polysulfides from Disulfides by Sulfur Insertion from S8 and an Unexpected Solvent Effect on the Product Distribution

“…Subsequent cleavage of the SÀ S bond of A resulting in the formation of a thiol-radical (RS * ) and a thiol-cation, which is stabilized by another disulfide molecule to form intermediate B is plausible (Scheme 4). [17] As the reaction takes place under anodic conditions only, reductive activation of sulfur seems not to be absolutely necessary. However, polysulfides were formed preferably in an undivided cell in a much higher extent as in a quasidivided cell [13] with a platinum wire as anode (Table 1, entry 20).…”

Electrochemical reactions of alkenes induced by anodic oxidation and their applications in organic synthesis

“…195,196 Electrolysis of alkenes in the presence of diselenides and disulfides is accompanied by hydroxy-, alkoxy-and acetamidoselenenation 196 ± 198 and acetamidosulfenation. 199 Hydroxy-, alkoxy-and acetamidoselenenation reactions are initiated by electrogenerated halogenonium ions. Under the action of these species, diphenyl diselenide and diphenyl sulfide are converted into phenylselenenyl and phenylsulfenyl halides.…”