title: Synthesis and elaboration of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane: a polar cyclohexane motif.
abstract: A stereocontrolled synthesis of all-cis-1,2,4,5- tetrafluoro-3-phenylcyclohexane is developed as the first functionalised example of this polar cyclohexane motif. The dipolar nature of the ring, arising due to two 1,3-diaxial C-F bonds, is revealed in the solid-state (X-ray) structure. The orthogonal conformation of the aryl and cyclohexyl rings in all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane, and in an ortho-nitro derivative, result in intramolecular (1h)JHF and (2h)JCF  NMR couplings relayed through hydrogen bonding. The aryl group of all-cis-1,2,4,5-tetrafluoro-3-phenylcyclohexane is elaborated in different ways to demonstrate the versatility of this compound for delivering the motif to a range of molecular building blocks.
authors.affiliation: School of Chemistry, University of St Andrews, North Haugh, St Andrews KY169ST (United Kingdom).
authors.forename: Alastair J
authors.initials: AJ
authors.lastname: Durie
authors.forename: Tomoya
authors.initials: T
authors.lastname: Fujiwara
authors.forename: Rodrigo
authors.initials: R
authors.lastname: Cormanich
authors.forename: Michael
authors.initials: M
authors.lastname: Bühl
authors.forename: Alexandra M Z
authors.initials: AM
authors.lastname: Slawin
authors.forename: David
authors.initials: D
authors.lastname: O'Hagan
mesh_terms: D003510:Cyclohexanes / Q000138:chemical synthesis* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation
chemical_list: D003510:Cyclohexanes; C506365:Cyclohexane
keywords: aromatic transformations; cyclohexane; fluorinations; organofluorine compounds; polar organic motifs