Iodomethylzinc iodide
Encyclopedia
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).
Iodomethylzinc iodide may also be generated by the reaction of diazomethane
with zinc iodide
, or by the reaction of methylene iodide with diethylzinc
.
Simmons-Smith reaction
The Simmons–Smith reaction is an organic cheletropic reaction in which a carbenoid reacts with an alkene to form a cyclopropane. It is named after Howard Ensign Simmons, Jr. and R. D. Smith...
. For example, iodomethylzinc iodide, formed in situ from diiodomethane
Diiodomethane
Diiodomethane or methylene iodide, commonly abbreviated "MI", is a liquid organoiodine compound. It is insoluble in water, but soluble in ether and alcohol. It has a relatively high refractive index of 1.741, and a surface tension of 0.0508 N·m−1...
and a zinc-copper couple
Zinc-copper couple
Zinc-copper couple is an alloy of zinc and copper that is employed as a reagent in organic synthesis. The “couple” was popularized after the report by Simmons and Smith in 1959 of its application as an activated source of zinc required for formation of an organozinc reagent in the Simmons-Smith...
reacts with cyclohexene
Cyclohexene
Cyclohexene is a hydrocarbon with the formula C6H10. This cycloalkene is a colorless liquid with a sharp smell. It is an intermediate in various industrial processes...
to give norcarane
Norcarane
Norcarane, or bicyclo[4.1.0]heptane, is a colorless liquid. It is an organic compound prepared using the Simmons-Smith reaction, by the action of diiodomethane and a zinc-copper couple on cyclohexene in diethyl ether....
(bicyclo[4.1.0]heptane).
Iodomethylzinc iodide may also be generated by the reaction of diazomethane
Diazomethane
Diazomethane is the chemical compound CH2N2. It is the simplest of diazo compounds. In the pure form at room temperature, it is a extremely sensitive explosive yellow gas, thus it is almost universally used as a solution in diethyl ether...
with zinc iodide
Zinc iodide
Zinc iodide is a chemical compound of zinc and iodine, ZnI2. The anhydrous form is white and readily absorbs water from the atmosphere. It can be prepared by the direct reaction of zinc and iodine in refluxing ether...
, or by the reaction of methylene iodide with diethylzinc
Diethylzinc
Diethylzinc 2Zn, or DEZn, is a highly pyrophoric organozinc compound consisting of a zinc center bound to two ethyl groups. This colourless liquid is an important reagent in organic chemistry and available commercially as a solution in hexanes, heptane, or toluene.-Synthesis:Edward Frankland first...
.