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

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