The emergence and properties of selectively fluorinated ‘Janus' cyclohexanes

David O'Hagan*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

1 Citation (Scopus)
6 Downloads (Pure)

Abstract

This account describes the evolution of a research programme that started by linking fluoromethylene (−CHF−) groups along aliphatic chains and then progressing to alicyclic rings with contiguous fluorine atoms. Different stereoisomers of aliphatic chains tend to adopt low polarity conformations. In order to force polar conformations, the programme began to address ring systems and in particular cyclohexanes, to restrain conformational freedom and co-aligned C−F bonds. The flagship molecule, all-cis-1,2,3,4,5,6-hexafluorocyclohexane 7, emerged to be the most polar aliphatic compound recorded. The polarity arises because there are three co-aligned triaxial C−F bonds and the six fluorines occupy one face of the ring. Conversely the electropositive hydrogens occupy the other face. These have been termed Janus face cyclohexanes after the Roman god with two faces. The review outlines progress by our group and others in preparing derivatives of the parent cyclohexane 7, in order to explore properties and potential applications of these Janus cyclohexanes.
Original languageEnglish
Article numbere202300027
Number of pages17
JournalThe Chemical Record
Volume23
Issue number9
Early online date4 Apr 2023
DOIs
Publication statusPublished - 8 Sept 2023

Keywords

  • Organofluorine compounds
  • Janus face cyclohexanes
  • Fluorine effects
  • Polar aliphatics
  • Fluorinated building blocks

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