Simmons-Smith Reaction

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Klein 23.4. Cyclopropanation of an alkene.

  • Reagents: CH2I2 and Zn(Cu). The reactive species is a carbenoid, not a free carbene students must draw in detail.
  • Stereochemistry: the addition is stereospecific. Cis alkenes give cis cyclopropanes.
  • One example, including an alkene that already has stereochemistry.