# Oxidative chlorination mechanism (sulfide to sulfonyl chloride)

I cannot find much guidance in the literature. Any ideas as to what the mechanism of this reaction might be?

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The mechanisms of oxidations of this type are often difficult to study since there are multiple pathways they can follow. For instance, I can draw valid-looking dipolar and radical mechanisms for this reaction. When I'm back in my office and have access to ChemDraw, I will post both as answers. –  Ben Norris Jun 28 '12 at 11:55
Regarding the species involved, $\ce{Cl_2}$ in water should disproportionate to $\ce{ClO^-}$, and possibly also create $\ce{CH_3COCl}$. If you think about this species as well, what reaction you can draw? –  ssavec Oct 30 at 7:55