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• Description

  Diphenyl disulfide is a colorless crystalline material with the formula (C6H5S)2 and often abbreviated Ph2S2. It is most commonly utilized as a reagent for integration of a phenylthio functionality into molecules. The phenylthio group in the compound has a useful function due to the numerous of reaction that it can facilitate in organic chemistry. Phenysulfides, for instance, undergo oxidative elimination, producing alkenes under relatively mild, normal conditions. Also phenyl sulfides can serve as a source of carbon-centered radicals in radical reactions.
  Diphenyl disulfide is usually synthesized by the oxidation of thiophenol:
  2 PhSH + I2 → Ph2S2 + 2 HI ;

• Reactions and Uses

  With Alkenes
  Ph2S2 adds cleanly to many dienes and alkenes upon catalysis by BF3.OMe2. The trifluoroacetoxysulfenylation of unsaturated esters, nitriles, amides, and carboxylic acids is possible with Ph2S2.
  As a Source of Thiiyl Radicals
  In the presence of radical initiators, upon thermolysis or photolysis, thiiyl radicals can be generated from PhSSPh. Therefore, the radicals generated add reversibly to alkynes and alkenes generating vinyl and alkyl radicals respectively (1).
  Reduction
  Ph2S2 undergoes reduction, which is a characteristic of disulfides. Hydride reagents such as super hydride and sodium borohydride can be used as reductants.
  Ph2S2 + 2 M → 2 MSPh (M = Li, Na, K) ;

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