Alkenyl Ditriflates and Diiodides: Conjugated, Non-Conjugated, and Cross-Conjugated
Leon Ruiz, Omar A.
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Theoretical studies of electrical conductivity in organic compounds suggests that conjugation of approximately one hundred alkenes will make an organic compound a super-conducting material. While a material with such extensive conjugation has never been prepared, synthetic studies are underway to identify procedures that can be incorporated to produce highly conjugated compounds. This study focuses on refining the synthetic methods available for this series of compounds that are of interest for the development of organic electrical conductors by establishing reproducibility, a satisfactory synthetic pathway, and spectral data for their identification. We report that conjugated and non-conjugated ditriflates were synthesized from diketones through thermodynamic and kinetic control, respectively. The vinyl triflates produced can be used to convert to other vinyl substrates by substitution and elimination methods. The ditriflates were purified and analyzed with column chromatography, recrystallization, and lH NMR spectroscopy. Also, a conversion from ditriflates to diiodides was attempted as a form of investigating the availability of the conversions.