Iodomethylzinc iodide is the active reagent in theSimmons–Smith reaction.[1] For example, iodomethylzinc iodide, formedin situ fromdiiodomethane and azinc-copper couple reacts withcyclohexene to givenorcarane (bicyclo[4.1.0]heptane).[1]
Iodomethylzinc iodide may also be generated by the reaction ofdiazomethane withzinc iodide, or by the reaction ofmethylene iodide withdiethylzinc.[1]