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1 article(s) from Rzepa, Henry S

The vicinal difluoro motif: The synthesis and conformation of erythro- and threo- diastereoisomers of 1,2-difluorodiphenylethanes, 2,3-difluorosuccinic acids and their derivatives

David O'Hagan,
Henry S. Rzepa,
Martin Schüler and
Alexandra M. Z. Slawin

Beilstein J. Org. Chem. 2006, 2, No. 19, doi:10.1186/1860-5397-2-19

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Scheme 1: Synthesis of vicinal dimethyl difluorosuccinates. The conversion of the tartrates 1 with SF₄ and HF ...

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Scheme 2: Schlosser's route to vicinal erythro- or threo- difluoro alkanes 5 [13].

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Scheme 3: Halofluorination of electron-rich alkenes with in situ fluoride displacement generates vicinal difl...

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Scheme 4: Bromofluorination of stilbene [19].

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Scheme 5: Treatment of anti-14 with base generated the E-fluorostilbene 15 by an anti elimination mechanism.

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Scheme 6: Hypothesis for the predominent retention of configuration during fluoride substitution via phenoniu...

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Scheme 7: Proposed C-C bond rotation during the preparation of 14 from cis-stilbene.

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Figure 1: Crystal structure of erythro-13.

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Figure 2: X-ray structure of threo-13.

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Figure 3: Expanded regions of the second order AA'XX' spin systems in the ¹H-NMR (left) and ¹⁹F-NMR spectra (...

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Figure 4: NMR coupling constants and calculated relative energies (kcalmol^-1) of the staggered conformers of ...

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Scheme 8: Synthesis of erythro-19 via ozonolysis of erythro-13.

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Figure 5: X-ray structure of erythro-19.

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Figure 6: X-ray structure of threo-19.

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Scheme 9: Strategy for the preparation of diastereoisomers of erythro- and threo- 20.

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Figure 7: NMR (CDCl₃, RT) coupling constants of erythro- and threo- 2,3-difluoro-3-phenylpropionates 21.

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Figure 8: Newman projections showing the staggered conformations of erythro- and threo- 21.

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Figure 9: X-ray structure of methyl threo- 21.

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Figure 10: The preferred conformation of α-fluoroamides has the C-F and amide carbonyl anti-planar [29,30].

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Scheme 10: The synthesis of stereoisomers of erythro- and threo- 22. These isomers could be separated by chrom...

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Figure 11: X-ray structure of erythro-22.

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Figure 12: Crystal packing of erythro-22 clearly indicating intermolecular hydrogen bonding.

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Figure 13: X-ray structure of threo-22.

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Figure 14: The conformations of erythro- and threo- 23 are very different as a consequence of each conformatio...

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Figure 15: ³J_HF and ³J_HH coupling constants for the erythro (yellow) and threo (blue) diastereoisomers of the ...

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Figure 16: Newman projections of the three staggered conformations of the erythro and threo stereoisomers of t...

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Figure 17: The average coupling constant with no conformational bias. The limiting coupling constants J_g = 8 H...

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Figure 18: The observed ³J_HF coupling constants are an average over the rotational isomers.

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Published 02 Oct 2006

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