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Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Mathew J. Jones, Ricardo Callejo, Alexandra M. Z. Slawin, Michael Bühl and David O'Hagan

Beilstein J. Org. Chem. 2016, 12, 2823–2827. https://doi.org/10.3762/bjoc.12.281

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Supporting Information File 1: Experimental part and NMR spectra of new synthesised compounds.
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Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring

Mathew J. Jones, Ricardo Callejo, Alexandra M. Z. Slawin, Michael Bühl and David O'Hagan

Beilstein J. Org. Chem. 2016, 12, 2823–2827. https://doi.org/10.3762/bjoc.12.281

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Jones, M. J.; Callejo, R.; Slawin, A. M. Z.; Bühl, M.; O'Hagan, D. Beilstein J. Org. Chem. 2016, 12, 2823–2827. doi:10.3762/bjoc.12.281

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TY  - JOUR
A1  - Jones, Mathew J.
A1  - Callejo, Ricardo
A1  - Slawin, Alexandra M. Z.
A1  - Bühl, Michael
A1  - O'Hagan, David
T1  - Organofluorine chemistry: Difluoromethylene motifs spaced 1,3 to each other imparts facial polarity to a cyclohexane ring
JF  - Beilstein Journal of Organic Chemistry
PY  - 2016///
VL  - 12
SP  - 2823
EP  - 2827
SN  - 1860-5397
DO  - 10.3762/bjoc.12.281
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.12.281
KW  - aliphatic rings
KW  - C–F bond
KW  - cyclohexane conformation
KW  - difluoromethylene group
KW  - organofluorine chemistry
N2  - 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.
ER  -

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