The synthesis of selectively fluorinated cyclohexanes will be described where single fluorine atoms are located on each carbon. In particular attention is paid to preparing single isomers where the fluorines are on one face of the cyclohexane ring and in the chair conformation they adopt 1,3-diaxial fluorine motifs. The preparation of all cis tetrafluorocyclohexyl motifs will be described, and the polar nature of these motifs will be illustrated. Their elaboration into pharmaceutical,  agrochemical and liquid crystalline relevant compounds will be demonstrated.  An ultimate challenge is to prepare a cyclohexane with a fluorine on each carbon and all of the six fluorine atoms 'up'. Such a ring system is predicted to be highly polar. Progress towards this target will be presented.

Selectively fluorinated cyclohexanes as polar fluoro-organic motifs

248th National Meeting (2014)

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