Synthesis and elaboration of All-cis-1,2,4,5-Tetrafluoro-3Phenylcyclohexane: a polar cyclohexane motif

Alastair J. Durie, Tomoya Fujiwara, Rodrigo Cormanich, Michael Buehl, Alexandra M. Z. Slawin, David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

25 Citations (Scopus)

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 CF 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)J(HF) and (2h)J(CF)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.

Original languageEnglish
Pages (from-to)6259-6263
Number of pages5
JournalChemistry - A European Journal
Volume20
Issue number21
DOIs
Publication statusPublished - 19 May 2014

Keywords

  • Aromatic transformations
  • Cyclohexane
  • Fluorinations
  • Organofluorine compounds
  • Polar organic motifs
  • SPECTRUM DEOXOFLUORINATING AGENT
  • ENHANCED THERMAL-STABILITY
  • SPACE HYDROGEN-FLUORINE
  • BIS(2-METHOXYETHYL)AMINOSULFUR TRIFLUORIDE
  • ORGANOFLUORINE CHEMISTRY
  • MEDICINAL CHEMISTRY
  • BOND ACCEPTOR
  • DEOXYFLUORINATION
  • CONFORMATION
  • NITRATIONS

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