Oxymercuration-Reduction: Hydration

Oxymercuration-Reduction:  Hydration

 

  • Markovnikov regiochemistry
  • Stereochemistry controlled by backside attack.
  • Evidence for this mechanism
    • No rearrangements observed
    • anti-addition stereochemistry product of oxymercuration.

 

Reduction

The organomercury compounds obtained from oxymercuration can be reduced with sodium borohydride (NaBH4).  The stereochemistry is lost during this step.