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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.