|Chapter 14: Organometallic Compounds|
Synthesis of Cyclopropanes using RZnX (The Simmons-Smith reaction)
Reaction type: 1. Oxidation-Reduction, 2. Addition
MECHANISM OF THE SIMMONS-SMITH REACTION
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.
|© Dr. Ian Hunt, Department of Chemistry, University of Calgary|