Attempts to oxidize sulfides under mechanochemical conditions: synthetic and stereochemical aspects

Abstract

Preliminary experiments devoted to the reaction of model sulfides with several oxidation reagents under mechanochemical conditions are presented. No reaction with sodium metaperiodate and (−)-(8,8-dichlorocamphorylsulfonyl)oxaziridine was observed. An interesting selectivity was observed in the oxidation reaction of aryl trifluoromethyl sulfides with hydrogen peroxide in the presence of tungstic phosphoric acid as a catalyst. Asymmetric induction has been observed during the oxidation of methyl phenyl sulfide to the corresponding sulfoxide carried out in the presence of d-camphorsulfonic acid or beta-cyclodextrin.

Graphical Abstract

Keywords:

• Mechanochemistry
• sulfides
• sulfoxides
• sulfones
• oxidation
• asymmetric synthesis
• selectivity