Molecular and solid state structure of the doubly-substituted ?-diketone 3,3'-bis(ferrocenylmethyl)pentane-2,4-dione

Guillermo Ahumada, Thierry Roisnel, Jean René Hamon, David Carrillo, CECILIA CAROLINA MANZUR NAZAL

Research output: Contribution to journalArticlepeer-review

1 Scopus citations

Abstract

ABSTRACT The ferrocene-containing ?-diketone, 3-ferrocenylmethyl-pentane-2, 4-dione 1, has been synthesized by reacting ferrocenyl methanol with acetylacetone in the presence of cerium(IV) ammonium nitrate as catalyst in C-C bond formation, and isolated as an orange oily product in 90% yield. The doubly-substituted 1,3-diketone, 3,3'-bis(ferrocenylmethyl)pentane-2,4-dione 2 was isolated as orange crystals in 79% yield, upon standing a dichloromethane solution of 1 at -30 C for two weeks. Both complexes have been authenticated by spectroscopic methods, mass spectrometry, and cyclic voltammetry. In addition, the molecular identity and geometry of 2 has been confirmed by single-crystal X-ray diffraction analysis. In the crystal lattice, the molecules pack as dimers through C-HO hydrogen bondings, where weaker C-Hp interactions link the dimeric units to form a chain structure.

Original languageEnglish
Pages (from-to)1963-1966
Number of pages4
JournalJournal of the Chilean Chemical Society
Volume58
Issue number4
DOIs
StatePublished - Dec 2013
Externally publishedYes

Keywords

  • 1,3-dione
  • Bimetallic complex
  • Catalyzed C-C coupling
  • Ferrocene
  • X-ray structure

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