Anodic oxidation of 1, n-halo(alkylthio)alkanes and 1, n-chloro(alkylsulfinyl)alkanes

Anodic oxidation of l, n-halo(alkylthio)alkanes [X-(CH2)n-S-R, X = CI, Br, I] and 1, n-halo(alkylsulfinyl)alkanes [CI-(CH2)n-S(0)-R] was studied by cyclic voltammetry in anhydrous acetonitrile and by controlled potential electrolyses. The ease of sulfur oxidation was not affected by the alkyl substituents R or the number of methylene groups n in compounds with n > 2. The oxidation of the 1, 2-halo(alkylthio)ethanes (n = 2) occurred at slightly higher potentials. The peak potentials decreased slightly in the order CI > Br > I which is probably due to the electronegativity of the halogen atoms. The investigated anodic oxidation was shown to be a two electron irreversible process. Electrolyses in aqueous acetronitrile led to the corresponding sulfoxides and sulfones in good yields.