ChemInform Abstract: Ring Opening of Cyclopropanemonocarboxylates and 1,1- Cyclopropanedicarboxylates Using Samarium(II) Diiodide (SmI2)-HMPA-THF System.
Abstract
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ChemInform Abstract
SmI2 efficiently promotes the regioselective ring opening of 2- substituted cyclopropanedicarboxylates (cf. (I)) to furnish the corresponding (2-substituted ethyl)malonates (II) in moderate to high yields under optimal conditions, regardless of the type of the 2- substituent. SmI2-mediated ring opening of cyclopropanemonocarboxylates bearing an aryl group at the 2-position proceeds in a similar regioselective fashion, whilst monocarboxylates bearing an aliphatic group at C-2 do not react with SmI2 at all under the same conditions. A plausible ring opening mechanism is proposed.