Abstract
2,2-Dimethyl-5-phenyl-1,1,3,3-tetrafluororocyclohexane has been prepared and characterised as an example of a facially polarised cyclohexane containing 1,3 related CF2 groups. The dipolar nature of the ring arises from the axial orientation of two of the C–F bonds pointing in the same direction, and set by the chair conformation of the cyclohexane. This electrostatic profile is revealed experimentally both in the solid-state (X-ray) packing of the rings and by solution (NMR) in different solvents. A computationally derived electrostatic profile of this compound is consistent with a more electronegative and a more electropositive face of the cyclohexane ring. This placing of CF2 groups 1,3 to each other in a cyclohexane ring is introduced as a new design strategy which could be applicable to the preparation of polar hydrophobic cyclohexane motifs.
Highlights
Selective incorporation of fluorine atoms is a powerful strategy for modulating the properties of organic compounds [1,2,3]
The dimethyldiketone 5c was prepared by double methylation of 5b [25] (Scheme 2)
The compound was prepared by direct difluorination of the corresponding α,α-dimethylated 1,3-diketone with DAST
Summary
Selective incorporation of fluorine atoms is a powerful strategy for modulating the properties of organic compounds [1,2,3]. The dipole moment associated with the C–F bond has rendered fluorine containing compounds important in the development of organic materials such as liquid crystals [8,9]. In our own lab we have been exploring the synthesis and properties of differently fluorinated aliphatic structures based on the cyclopentane (1) and cyclohexane (2 and 3) rings, compounds which can show quite large dipole moments depending on the stereochemistry [19,20] (Figure 1).
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