Subscribe to RSS
DOI: 10.1055/s-0034-1378471
Two Sides to this Story: All-cis-1,2,4,5-tetrafluoro-3-arylcyclohexanes
Publication History
Publication Date:
18 July 2014 (online)
Significance
The authors adapt their recent synthesis of an all-cis tetrasubstituted cyclohexane (Chem. Commun. 2012, 48, 9643) to allow attachment of this group to other functionalities. By starting with biphenyl and employing a Birch reduction, they are able to carry out their fluorination on 3-phenyl-1,4-cyclohexadiene, resulting in the same all-cis tetrasubstitution but with an appended functionalizable phenyl ring. Using electrophilic aromatic substitution, they are able to add various functional groups to the ring, although it is notable that selectivity is low due to the only weakly directing nature of the tetrafluorocyclohexyl group.
#
Comment
This two-sided cyclohexyl group features oriented C–F bonds, providing the molecule with an inherent polarity. This can even be observed in solution-state NMR experiments, where interaction of the fluorines with aromatic solvents causes a distinct shift in the 1H NMR resonances of the other side of the ring. The current work makes important strides towards making the tetrafluorocyclohexyl group available as a building block by introducing synthetic handles for incorporating this moiety into molecular designs.
#
#