Abstract
[reaction: see text] The aminochlorination of methylenecyclopropanes (MCPs) 1 and vinylidenecyclopropanes (VCPs) has been explored with use of FeCl(3) (20 mol %) as a Lewis acid catalyst in acetonitrile under convenient mild conditions. The stereochemistry has been unambiguously confirmed by X-ray structural analysis. The aziridinium-based mechanism, accounting for both regio- and stereoselectivity, has been carefully studied. A linear free-energy relationship study of this reaction confirms consistency with the Hammet equation.
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