The cyclohexane motif is among the most common in organic chemistry but selectively fluorinated versions are rare. The high polarity of C–F bonds can influence the conformation and reactivity of molecules, making fluorinated molecules high on the target list of many chemists, including David O’Hagan at the University of St Andrews, UK.
His team have managed to make 1,2,3,4-tetrafluorocyclohexane, the first example of a cyclohexane with more than two vicinal fluorine atoms. The all syn stereochemistry forces two of the C–F bonds into 1,3-diaxial orientations. This diaxial interaction makes the molecule polar, which O’Hagan suggests could make it a novel polar structural motif for organic materials.
Find out more: download O’Hagan’s ChemComm communication for free until 28th July.
Also of interest: Fluorine chemistry web theme
