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 (bicycloheptane).
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 .
References
^ Smith, R. D.; Simmons, H. E. "Norcarane" . Organic Syntheses ; Collected Volumes , vol. 5, p. 855
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