Energetics of fluoroalkene double bond isomerizations

PE Lindner, DM Lemal

Index: Lindner, Patrick E.; Lemal, David M. Journal of the American Chemical Society, 1997 , vol. 119, # 14 p. 3267 - 3273

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Citation Number: 12

Abstract

The effects of perfluorination of cyclic and acyclic alkenes have been examined. Quantum mechanical calculations and experimental data show that vicinally substituted acyclic alkenes are strongly destabilized by fluorination. Quite surprisingly, the destabilization is much smaller for cyclic analogs. This difference has dramatic consequences for the relative stabilities of double bond isomers in cyclic and acyclic systems, including keto-enol ...