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Isomerization of 1,1,2,3,3-pentafluoro-1,5-hexadiene upon reaction with fluoride ions. First example of sequential anionotropic and prototropic allylic rearrangements

  • T. I. Gorbunova
  • M. I. Kodess
  • T. G. Khonina
  • T. I. Filyakova
  • A. V. Podol'skii
  • V. I. Saloutin
Organic Chemistry Chemical Transformations Of Organic Compounds

Abstract

Upon heating in DMF medium with KF and 18-crown-6 1,1,2,2,3-pentafluoro-1,5-hexadiene (1) is converted to 4,5,6,6,6-pentafluoro-1,3-hexadiene and 1,1,1,2,3-pentafluoro-2,4-hexadiene. Reaction of (1) with KHF2 results in the formation of its HF addition product, namely, 4,4,5,6,6,6-hexafluoro-1-hexene. We assume that the driving force in the isomerization of (1) is the formation of conjugated products, involving both the fluorinated and nonfluorinated portions of the molecules, preferably with the minimum number of fluorine atoms attached to the double bond.

Keywords

nonconjugated polyfluorinated dienes allylic rearrangement nucleophilic isomerization hydrosilylation hydrofluorination 

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Copyright information

© Plenum Publishing Corporation 1992

Authors and Affiliations

  • T. I. Gorbunova
  • M. I. Kodess
  • T. G. Khonina
  • T. I. Filyakova
  • A. V. Podol'skii
  • V. I. Saloutin

There are no affiliations available

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