Iodomethylzinc iodide

Iodomethylzinc iodide is the active reagent in the Simmons–Smith reaction.[1] 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).[1]

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.[1]

References
  1. Smith, R. D.; Simmons, H. E. "Norcarane". Organic Syntheses.; Collective Volume, 5, p. 855
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