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Electrochemical oxidation of O‐(4‐chlorobenzyl) S‐methyl dithiocarbonate using tris(2,4‐dibromophenyl)amine as a redox mediator was studied by cyclic voltammetric measurements. The triarylamine mediated anodic fluorodesulfurization of O‐(4‐chlorobenzyl) and O‐(4‐bromobenzyl) S‐methyl dithiocarbonates provided 4‐chloro‐ and 4‐bromobenzyl fluorides, respectively in moderate yields. On the other hand, similar anodic fluorination of O‐(2‐phenethyl) S‐octyl dithiocarbonate and O‐(4‐bromophenyl) S‐methyl dithiocarbonate afforded 2‐phenethyl trifluoromethyl ether and difluoro(methylthio)methyl 4‐bromophenyl ether, respectively. Mechanistic aspects are also discussed.

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