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Beilstein J. Org. Chem. 2016, 12, 2823–2827, doi:10.3762/bjoc.12.281
Selected fluorinated polar alicyclic scaffolds.
Retrosynthetic plan to the preparation of 1,1,3,3-tetrafluorocyclohexane structures.
Preparation of starting materials 5c and 6a–c.
Deoxofluorination of diketones 5. Reagents and conditions: a) DAST, DCM, rt, overnight, 4a (traces)...
Fluorodesulfurisation of bis-dithianes 6. Reagents and conditions: a) NIS, HF·Py, DCM, −78 °C to rt...
X-ray structure of compound 4c. The image shows two molecules stacked with the non-fluorine face po...
1H NMR spectra of 4c. A) shows the spectrum in [2H8]-toluene, and B) shows the spectrum in chlorofo...
Electrostatic potential map for 4c calculated at the B3LYP/6-311G(d,p) level for an optimised struc...
Beilstein J. Org. Chem. 2014, 10, 18–25, doi:10.3762/bjoc.10.4
The CF2 group in 1c accelerates RCM reactions relative to CHF (1d) and CH2 (1e) and with a similar ...
X-ray structures of a) 1,1,4,4- (3) b) 1,1,7,7- (4) and c) 1,1,6,6- (5) tetrafluorocyclododecanes. ...
Synthesis targets: Palmitic acid analogues 6a–c.
Synthesis route to 8,8-difluorohexadecanoic acid (6a).
The synthesis of palmitic acid analogues 6b and 6c.
DSC traces for the three palmitic acid analogues 6a–c.
The X-ray crystal structures of 8,8-difluorohexadecanoic acid (6a).
The X-ray structure of 8,8,11,11-tetrafluorohexadecanoic acid (6c).
Synthesis route to the tetrafluorinated alkane 27.
The X-ray structure of 8,8,11,11-tetrafluorononadecane (27).
Conformational interconversion of 1,4-di-CF2 motif.