Iodomethylzinc iodide

Iodomethylzinc iodide is the active reagent in the Simmons–Smith reaction. For example, iodomethylzinc iodide, formed in situ from diiodomethane and a zinc-copper couple reacts with cyclohexene to give norcarane (bicyclo[4.1.0]heptane).


 * [[Image:Simmons-Smith cyclohexene to bicyclo-4.1.0-heptane.svg|center|300px|An example of the Simmons-Smith reaction]]

Iodomethylzinc iodide may also be generated by the reaction of diazomethane with zinc iodide, or by the reaction of methylene iodide with diethylzinc.