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]

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. ^ a b c Smith, R. D.; Simmons, H. E., "Norcarane", Org. Synth., http://www.orgsyn.org/orgsyn/orgsyn/prepContent.asp?prep=cv5p0855 ; Coll. Vol. 5: 855