Picture of neon light reading 'Open'

Discover open research at Strathprints as part of International Open Access Week!

23-29 October 2017 is International Open Access Week. The Strathprints institutional repository is a digital archive of Open Access research outputs, all produced by University of Strathclyde researchers.

Explore recent world leading Open Access research content this Open Access Week from across Strathclyde's many research active faculties: Engineering, Science, Humanities, Arts & Social Sciences and Strathclyde Business School.

Explore all Strathclyde Open Access research outputs...

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

Full text not available in this repository. Request a copy from the Strathclyde author

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.