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Beilstein J. Org. Chem. 2016, 12, 2823–2827, doi:10.3762/bjoc.12.281
Graphical Abstract
Figure 1: Selected fluorinated polar alicyclic scaffolds.
Scheme 1: Retrosynthetic plan to the preparation of 1,1,3,3-tetrafluorocyclohexane structures.
Scheme 2: Preparation of starting materials 5c and 6a–c.
Scheme 3: Deoxofluorination of diketones 5. Reagents and conditions: a) DAST, DCM, rt, overnight, 4a (traces)...
Scheme 4: Fluorodesulfurisation of bis-dithianes 6. Reagents and conditions: a) NIS, HF·Py, DCM, −78 °C to rt...
Figure 2: X-ray structure of compound 4c. The image shows two molecules stacked with the non-fluorine face po...
Figure 3: 1H NMR spectra of 4c. A) shows the spectrum in [2H8]-toluene, and B) shows the spectrum in chlorofo...
Figure 4: Electrostatic potential map for 4c calculated at the B3LYP/6-311G(d,p) level for an optimised struc...