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Simmons-Smith Cyclopropanation Reaction
The Simmons-Smith cyclopropanation reaction is a classic method used to install a cyclopropane moiety from a parent alkene. The reaction is typically conducted using diiodomethane in combination with metallic zinc and copper (Zn/Cu). Zn/Cu can be replaced with diethylzinc, which is known as the Furukawa modification.1) The Simmons-Smith reaction has considerable advantages over other cyclopropanation methods as it does not require the use of the highly hazardous diazomethane. In addition, the reaction has a wide functional group tolerance including with alkynes, carbonyls, alcohols, ethers, and others and it proceeds stereospecifically.
- Reagents:
- Diiodomethane, Zn/Cu, Diethylzinc
- Reactants:
- Alkenes
- Products:
- Cyclopropanes
- Scheme:
-
- 1) A novel route to cyclopropanes from olefins
- 2) Reaction of dilithiated carboxylic acids with iodine: evidence for the formation of a radical anion intermediate
- 3) Gold(I)-Catalyzed Ring Expansions of Unactivated Alkynylcyclopropanes to (E)-2-Alkylidenecyclobutanamines in the Presence of Sulfonamides
- Original literature:
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- A NEW SYNTHESIS OF CYCLOPROPANES FROM OLEFINS
- Review literature:
-
- Simmons-Smith Cyclopropanation Reaction
