Starting from ( S )- S- ferrocenyl- S -4-tolyl sulfoxide the planar-chiral imidazolium salt ( R p )-1-[2-(trimethylsilyl)ferrocenylmethyl]-3-methylimidazolium iodide was synthesized utilizing the directed ortho -metalation strategy. Deprotonation thereof yielded the first planar-chiral carbene, ( R p )-3-methyl-1-[2-(trimethylsilyl)ferrocenylmethyl]imidazolin-2-ylidene, which is stable in tetrahydrofuran at room temperature for several hours. Conversion with sulfur resulted in the formation of the corresponding thiourea derivative. Reaction with the metal precursors [Rh(COD)Cl] 2 and Cr(CO) 6 gave air-stable complexes. For the latter product an X-ray structural analysis was conducted.
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Bolm et al. (2002) studied this question.
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