Cyclopropyllithium is an organolithium reagent that can be used to synthesize various cyclopropyl derivatives, to synthesize five-membered nitrogen heterocyclic compounds via cyclopropylimine rearrangement, and to synthesize cyclopentene via vinylcyclopropane rearrangement.
Cyclopropyllithium is usually prepared by reacting finely divided lithium with cyclopropyl chloride or cyclopropyl bromide in ethereal solution. The reaction can also be carried out in pentane.
Solutions of organolithium reagents are highly flammable and moisture sensitive. Appropriate precautions are recommended. Use in a fume hood. Stability of cyclopropyllithium in ether is similar to that of n-Butyllithium, whereas in THF its stability is greater.
