Issue 12, 1982

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.

Article information

Article type
Paper

J. Chem. Soc., Chem. Commun., 1982, 658-659

The feeble nucleofugality of a nitronate leaving group and its enhancement by ring strain

P. P. Piras, P. J. Thomas and C. J. M. Stirling, J. Chem. Soc., Chem. Commun., 1982, 658 DOI: 10.1039/C39820000658

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