Mechanistic aspects of the isomerization of Z-vinylic tellurides double bonds in the synthesis of potassium Z-vinyltrifluoroborate salts
2008

Isomerization of Z-vinylic Tellurides in Potassium Vinyltrifluoroborate Synthesis

publication Evidence: moderate

Author Information

Author(s): Stefani Hélio A, Guadagnin Rafael C, Keppler Artur F, Botteselle Giancarlo V, Comasseto João V, Suganuma Carlos A

Primary Institution: Faculdade de Ciências Farmacêuticas, Universidade de São Paulo, São Paulo, Brazil

Hypothesis

The study investigates the mechanism of isomerization of Z-vinylic tellurides during the synthesis of potassium vinyltrifluoroborate salts.

Conclusion

The study identified radical species that promote the stereoinversion of vinylic compounds during the preparation of potassium vinyltrifluoroborate salts.

Supporting Evidence

  • The study presents the first reported preparation of potassium E-vinyltrifluoroborate salts from Z-vinylic tellurides.
  • EPR experiments confirmed the presence of radical species during the reaction.
  • Control experiments demonstrated that the generation of nBuBF3K salt is dependent on the presence of nBuTenBu.

Takeaway

The researchers found that certain chemicals can change shape during a reaction, which helps make new compounds.

Methodology

The study used EPR spin trapping experiments to identify radical species involved in the reaction mechanism.

Digital Object Identifier (DOI)

10.1186/1860-5397-4-9

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