1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies

Joseph Alia, Nancy E. Carpenter, Amanda J. Albrecht, Sharon Alexander, Taylir L. Bullick, Andrew J. Helmin, Scott A. Hubers, Daron E. Janzen, Jordan T. Koehn, Bethany Nyland, Laura Thoma, Lynn Weyer, Josh Wurst, Benjamin E. Kucera

    Research output: Contribution to journalArticle

    Abstract

    Advanced precursors to novel ferrocene-based ligands Cp2FeC(O)CH(R)C(O)CH3 (R = benzyl, allyl) were synthesized from 1-ferrocenylbutane-1,3-dione via active methylene chemistry. Crystal structures were obtained and computational studies carried out to explore the structural features of these new compounds. Addition of carbonyl electrophiles resulted in the formation of unexpected products, which were identified and mechanisms for their formation proposed.

    Original languageEnglish (US)
    Article number114378
    JournalPolyhedron
    Volume180
    DOIs
    StatePublished - Apr 1 2020

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    Keywords

    • Alkylation
    • Butane-1,3-dione
    • Chiral ligands
    • Ferrocene
    • NBO analysis
    • Organometallic synthesis
    • Retro-Claisen

    Cite this

    Alia, J., Carpenter, N. E., Albrecht, A. J., Alexander, S., Bullick, T. L., Helmin, A. J., Hubers, S. A., Janzen, D. E., Koehn, J. T., Nyland, B., Thoma, L., Weyer, L., Wurst, J., & Kucera, B. E. (2020). 1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies. Polyhedron, 180, [114378]. https://doi.org/10.1016/j.poly.2020.114378