Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
1322687 | Journal of Organometallic Chemistry | 2013 | 5 Pages |
•Reaction between biacetyl:trimethylphosphite adduct and ferrocenecarboxaldehyde.•1-(4-Methyl-2,5-diferrocenyl-1,3-dioxolan-4-yl)ethanone as single diastereomer.•Characterization by elemental analysis, IR and 2D NMR, and cyclic voltammetry.•Crystal structure of the compound determined by X-ray diffraction analysis.
Reacting an 1:1 stoichiometric molar ratio of ferrocenecarboxaldehyde and 2,2,2-trimethoxy-4,5-dimethyl-1,3,2-dioxaphospholene, neat, at room temperature for one week, leads to the diastereoselective formation of a bis-ferrocenyl 1,3-dioxolane complex 1-(4-methyl-2,5-diferrocenyl-1,3-dioxolan-4-yl)ethanone (1), in 30% isolated yield. The compound has been fully characterized by FT-IR, mono- and two-dimensional 1H and 13C NMR spectroscopy, elemental analysis, and cyclic voltammetry. Complex 1 has also been characterized by single crystal X-ray analysis.
Graphical abstractReaction of equimolar amounts of biacetyl trimethylphosphite 1:1 adduct and ferrocenecarboxaldehyde, at room temperature for one week in a solventless process, affords the unexpected bis-ferrocenyl dioxolane derivative, 1-(4-methyl-2,5-diferrocenyl-1,3-dioxolan-4-yl)ethanone (illustrated), formed as a single diastereoisomer.Figure optionsDownload full-size imageDownload as PowerPoint slide