(SR,1R,2S)-1-(tert-Butylsulfinyl)2-(hydroxymethyl)ferrocene

From the reaction of (SR)-(-)-tert-butylsulfinylferrocene with (2,4,6-triisopropylphenyl)lithium followed by paraformaldehyde, the title compound, [Fe(C₅H₅)(C₁₀H₁₅O₂S)], was obtained as an unexpected by-product along with the major product, (SR,1S,2R)-2-(tert-butylsulfinyl)ferrocenylmethanol. The absolute structure of this by-product could not be ascertained via NMR, but it was characterized by X-ray diffraction as (SR,1R,2S)-2-(tertbutylsulfinyl)ferrocenylmethanol, a diastereoisomer of the major product. The two cyclopentadienyl rings are rotated away from one another by 25.5 (5)° (from an eclipsed form towards a gauche form), in contrast to the mutually eclipsed rings generally found in monosubstituted ferrocenes. Hydrogen bonding between sulfoxide O atoms and hydroxyl H atoms produces infinite one-dimensional chains.

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