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The Strathprints institutional repository is a digital archive of University of Strathclyde's Open Access research outputs. Strathprints provides access to thousands of Open Access research papers by University of Strathclyde researchers, including by researchers from the Department of Computer & Information Sciences involved in mathematically structured programming, similarity and metric search, computer security, software systems, combinatronics and digital health.

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Syntheses of selectively fluorinated cyclodecenones: the first deployment of the neutral oxy-cope rearrangement in organofluorine chemistry

Percy, J.M. and Hursthouse, M.B. and Spencer, N.S. and Tolley, M. and DiMartino, G. and Light, M.E. (2003) Syntheses of selectively fluorinated cyclodecenones: the first deployment of the neutral oxy-cope rearrangement in organofluorine chemistry. Organic and Biomolecular Chemistry, 1 (24). pp. 4423-4434. ISSN 1477-0520

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Abstract

Metallated haloalkenes were used to open epoxides in moderate to good yield. The homoallylic alcohols obtained underwent Swern oxidation to afford three γ,γ-difluorinated β,γ-enones, which reacted with either vinyllithium, 2-lithio-2H-dihydropyran or another metallated haloalkene to afford substituted trans-1,2-divinylcyclohexanols of different degrees of stability. These intermediates underwent neutral thermal oxy-Cope rearrangements when heated in xylene in Ace® tubes. The first-formed enols ketonised without loss of HF to afford a range of cyclodecenones in moderate to good yield; X-ray crystallography was used extensively for product characterisation. All substrates rearranged more rapidly than a cis/trans mixture of 1,2-divinylcyclohexanols.