Two substrates, three products: Reactions between ferrocene-carboxaldehyde and dioxaphospholene, characterization and crystal structures of oxygenated C3- and C4-chain-containing ferrocenes

Guillermo Ahumada, Paul Hamon, Vincent Dorcet, Thierry Roisnel, Carolina Manzur, David Carrillo, Juan Pablo Soto, Jean René Hamon

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

Reactions of aldehydes RCHO with 2,2,2-trimethoxy-4,5-dimethyl-1,3,2- dioxaphospholene are known to form trimethylbiacetyl-aldehyde-phosphite adducts which upon methanolysis gave rise to the corresponding symmetrical 3-R-2,4-pentanediones (R = aryl, alkyl). Reactions between ferrocenecarboxaldehyde and the biacetyl-trimethylphosphite adduct, whatever the experimental conditions used, afforded three new oxygenated C3 and C4 side-chain containing ferrocenyl complexes, namely, 1-ferrocenyl-1,2-propanedione (1, Fc-C(O)C(O)CH3; Fc = (η5-C5H5)Fe(η5-C 5H4)), 4-methoxy-4-ferrocenyl-3-hydroxy-3-methyl-2- butanone (2, Fc-CH(OCH3)C(CH3)(OH)C(O)CH3) as a single diastereoisomer, and the ferrocenyl enone 4-ferrocenyl-3-methyl-3-buten- 2-one (3, Fc-CHC(CH3)C(O)CH3) with the enone portion adopting the s-trans conformation in the solid state. The compounds readily purified by silica gel packed column chromatography were isolated in 31-44% yields, and their constitution is in agreement with elemental analyses, IR and multinuclear NMR spectroscopy, and electrospray mass spectrometry. Their molecular identity and geometry have been confirmed by single-crystal X-ray diffraction.

Original languageEnglish
Pages (from-to)40-46
Number of pages7
JournalJournal of Organometallic Chemistry
Volume732
DOIs
StatePublished - 15 May 2013
Externally publishedYes

Keywords

  • Enone
  • Ferrocene
  • Hydroxyketone
  • X-ray structure
  • α-Diketone

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