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Oxidation of Sulfides to Sulfoxides and Sulfones

Oxidation of Sulfides to Sulfoxides and Sulfones: Mechanism

  • Oxidation of sulfide to sulfoxide.In the first step of the reaction, the sulfur atom attacks the terminal oxygen of the peroxide group. Breakage of the peroxide bond results in the formation of an alkoxy anion and a sulfoxide protonated at the oxygen atom. Proton exchange yields the sulfoxide and the alcohol corresponding to the peroxide.
Fig.1
  • Oxidation of sulfoxide to sulfone.In acidic or neutral solution, the oxidation follows the same mechanism as that described for the oxidation of sulfide to sulfoxide. In basic solution, however, a nucleophilic attack of the peroxy anion takes place at the sulfur atom.
Fig.2

This oxidation is somewhat slower than the oxidation of sulfides.

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