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Synthesis of Cyclopropanes using RZnX (The Simmons-Smith reaction)

Cyclopropanation using the Simmons-Smith reaction

Reaction type:  1.  Oxidation-Reduction,  2.   Addition

Summary

Simmons-Smith reaction is stereospecific
Related reactions  
MECHANISM OF THE SIMMONS-SMITH REACTION
Step 1:
A concerted reaction : both new C-C are formed simultaneously. Best viewed as the nucleophilic C=C causing loss of the iodide leaving group and the electrons from the nucleophilic C-Zn bond being used to form the other C-C bond.
cycloaddition mechanism of the Simmons-Smith
 

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© Dr. Ian Hunt, Department of Chemistry, University of Calgary