The feeble nucleofugality of a nitronate leaving group and its enhancement by ring strain
Abstract
The rank of a nitronate ion in activated alkene-forming elimination is low (+2.6); incorporation of the leaving goup in a cyclopropane accelerates elimination so much that the (ElcB)R–(ElcB)I borderline is traversed but the retro-Thorpe–Ingold effect nevertheless operates.