Reaction between ferrocene-carboxaldehyde and dioxaphospholene: Characterization and crystal structures of an unexpected bisferrocenyldioxolane

• 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.

Reaction 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 as PowerPoint slide