Kinetics of the Thermal Exchange between Iodine and Allyl Iodide

Synthesis of β,γ-Unsaturated Lactams via a Magnesium Iodide Promoted Ring Expansion of Secondary Methylenecyclopropyl Amides

“…Although we note that either pathway is possible, orbital constraints favor an S N 2 mechanism. Iodide-mediated isomerization of the intermediate allylic iodide , would then account for the observation that both the exo methylene-substituted and cyclopropyl-substituted starting materials give the same product (Table , entries 1 and 2). Enolate protonation and cyclization of 7 or 8 10 then affords the observed products, although the relative order of these two steps may depend on the electronic properties of the aromatic group.…”