Reactions of fluorinated cyclobutenes with grignard reagents

Park, J.D.; CROFT, T. S.; ANDERSON, R. W.

doi:10.1016/s0022-328x(00)93026-2

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1997

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Cited by 8 publications

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“…Cope rearrangement should make it possible to equilibrate the double bond in each system as shown below. Dienes 6 and 8 ( E and Z ) were prepared by the reaction of the Grignard reagent from 4-bromo-1-butene with perfluorocyclobutene and ( E )- and ( Z )-perfluoro-2-butene (4:1), respectively . When a mixture of ( Z )- 8 and ( E )- 8 (1.3:1.0) was heated in a sealed ampule at 300 °C for 3 h, Cope rearrangement took place smoothly to diene 7 .…”

Section: Resultsmentioning

confidence: 99%

Energetics of Fluoroalkene Double Bond Isomerizations

Lindner

Lemal

1997

J. Am. Chem. Soc.

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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 systems. The reasons for the contrast are discussed in detail.

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Section: Resultsmentioning

confidence: 99%