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Synlett 1997; 1997(5): 571-573
DOI: 10.1055/s-1997-3224
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Improved Difluorination of Cyclohexenones using Morph-DAST by the Application of Ultra-High Pressure

Julian M. Box1 , Laurence M. Harwood2 , Roger C. Whitehead3
  • 1Department of Chemistry, Reading University, Whiteknights, Reading, RG6 6AD, U.K., Telephone +44 (0)1189 318449; Fax +44 (0)1189, 316782
  • 2Department of Chemistry, Reading University, Whiteknights, Reading, RG6 6AD, U.K., Telephone +44 (0)1189 318449; Fax +44 (0)1189, 316782, Email L.M.Harwood@reading.ac.uk
  • 3Department of Chemistry, Reading University, Whiteknights, Reading, RG6 6AD, U.K., Telephone +44 (0)1189 318449; Fax +44 (0)1189, 316782, Email R.C.Whitehead@reading.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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2,6- and 6,6- difluorinated α-substituted cyclohexenes have been prepared by the action of morpholinosulfur trifluoride on the corresponding cyclohex-2-enones under thermal conditions. The overall efficiency of this process has been significantly improved by the application of ultra high pressure (10-19Kbar). Investigations into the scope of this methodology have resulted in the preparation of the novel fluorinated compounds: 6,6-difluorolimonene and 3,3-difluoro-4-cholestene.

morph-DAST - gem-difluorination - ultra high pressure