Synthesis and Conformation of Difluoro Compounds
Author Information
Author(s): O'Hagan David, Rzepa Henry S, Schüler Martin, Slawin Alexandra M Z
Primary Institution: University of St Andrews
Hypothesis
The study explores how the conformation of erythro- and threo- diastereoisomers of difluoro compounds is influenced by the fluorine gauche effect.
Conclusion
The study demonstrates that the overall chain conformations of the 2,3-difluorosuccinates diastereoisomers are influenced by the fluorine gauche effect.
Supporting Evidence
- The study highlights the prospects of utilizing the vicinal difluorine motif as a tool for influencing the conformation of organic molecules.
- The fluorine gauche effect was shown to significantly influence the conformation of the 1,2-difluorosuccinates.
- Different synthetic routes were explored to prepare diastereomerically pure samples of the compounds.
Takeaway
This research shows that certain chemical structures can change shape based on how their atoms are arranged, especially when fluorine atoms are involved.
Methodology
The study involved synthesizing 2,3-difluorosuccinates and assessing their conformations using X-ray crystallography and NMR, along with ab initio calculations.
Limitations
The study faced challenges in synthesizing certain isomers and achieving high yields.
Digital Object Identifier (DOI)
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