section_path: Chemical reactions
section_name: Chemical reactions
paragraph_text: Chemical reactions
  
  It is used is for the production of borane dimethyl sulfide from diborane:
  
  Oxidation of dimethyl sulfide gives the solvent dimethyl sulfoxide. Further oxidation affords dimethyl sulfone.
  
  As illustrated above by the formation of its adduct with borane, dimethyl sulfide is a Lewis base. It is classified as a soft ligand (see also ECW model). It forms complexes with many transition metals but such adducts are often labile. For example, it serves a displaceable ligand in chloro(dimethyl sulfide)gold(I).
  
  Dimethyl sulfide is used in the workup of the ozonolysis of alkenes. It reduces the intermediate trioxolane. The Swern oxidation produces dimethyl sulfide by reduction of dimethylsulfoxide.
  
  With chlorinating agents such as sulfuryl chloride, dimethyl sulfide converts to chloromethyl methyl sulfide:
  
  Like other methylthio compounds, DMS is deprotonated by butyl lithium: