Simmons-Smith Reagent (Et₂Zn, CH₂I₂): An Efficient Reagent in Organic Synthesis

Introduction

The diethylzinc/diiodomethane or zinc-diiodomethane (Et₂Zn, CH₂I₂ or Zn, CH₂I₂ = ICH₂ZnI) known as Simmons-Smith reagent is probably the best known carbenoid reagent in organic syntheses. [¹] This ether soluble reagent has been used mainly for the conversion of al­kenes into cyclopropanes [¹] via stereospecific and supra­facial CH₂ addition using chiral auxiliaries, [²] reagents [³] and catalysts. [4]

Due to the presence of cyclopropanes in many biologically and medicinally important molecules, [5] natural products, [6] essential oils [7] and the marine cyanobacteriums, [8] some recent applications of Simmons-Smith reagent are reported herein.

References

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