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 journalArticlepeer-review

    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

    Bibliographical note

    Funding Information:
    We thank Dr. Christopher Schwartz for assistance in analysis of 1H NMR spectral data for 2b, and Mark Raths of Willie's SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF?MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University. This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds.

    Funding Information:
    This work was supported in part by the University of Minnesota Undergraduate Research Opportunities Program and the University of Minnesota Morris Faculty Research Enhancement Funds .

    Funding Information:
    We thank Dr. Christopher Schwartz for assistance in analysis of 1 H NMR spectral data for 2b , and Mark Raths of Willie’s SuperValu (Morris, MN) for donations of dry ice. The authors gratefully acknowledge St. Catherine University and NSF–MRI award No. 1125975, MRI Consortium: Acquisition of a Single Crystal X-ray Diffractometer for a Regional PUI Molecular Structure Facility. DEJ acknowledges the Carondelet Scholars program supported by St. Catherine University.

    Publisher Copyright:
    © 2020 Elsevier Ltd

    Keywords

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

    Fingerprint Dive into the research topics of '1-Ferrocenylbutane-1,3-dione as a scaffold for ferrocenyl-based ligands: Synthesis, X-ray and computational studies'. Together they form a unique fingerprint.

    Cite this