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A number of organometallic stilbenes of the general type [Co(eta4-C4Ph4)(eta5-C 5H4CHCHR] are reported where R is C6H 4X-4 (X = H, OMe, Br, NO2), 1-naphthyl, 9-anthryl, 1-pyrenyl, (eta5-C5H4)Co(eta4- C4Ph4), and (eta5-C5H 4)Fe(eta5-C5H4Y) {Y = CHO, CHC(CN)2 and CHCHC5H4-eta5) Co(eta4-C4Ph4)}. They were prepared by Wittig or Horner-Wadsworth-Emmons reactions which yield both E and Z or only E products respectively. The isomers were separated and all compounds characterised by standard spectroscopic techniques as well as by X-ray diffraction methods in many cases. The electrochemistry of the stilbene analogues in dichloromethane solution is also reported. In most, the (eta5-C5H4)Co(eta4-C 4Ph4) functional group undergoes a reversible one-electron oxidation. For those molecules that also include (eta5-C 5H4)Fe(eta5-C5H4Y), this is preceded by the reversible oxidation of the ferrocenyl group. Spectroscopic and structural data suggests that for most compounds there is little electronic interaction between Co(eta4-C4Ph 4)(eta5-C5H4) and the R end groups which are effectively independent of one another. The only exceptions to this are Z and E-[Co(eta4-C4Ph4) (eta5-C5H4CHCHC6H 4NO2-4], and [Co(eta4-C4Ph 4)(eta5-C5H4CHCHC 5H4-eta5)Fe{eta5-C 5H4CHC(CN)2}] where the electronic spectra are respectively consistent with a significant Co(eta4-C 4Ph4)(eta5-C5H4)/ NO2 donor/acceptor interaction and a less significant Co(eta4-C4Ph4)(eta5-C 5H4)/C(CN)2 one. However, OTTLE studies show that in the electronic spectra of [Co(eta4-C4Ph 4)(eta5-C5H4CHCHR]+ there are low energy absorption bands (950-1800 nm) which are attributed to R ? Co(eta4-C4Ph4)(eta5- C5H4)+ or, when R is a ferrocenyl-base group, Co(eta4-C4Ph4)(eta5-C 5H4) ? (eta5-C5H 4)Fe(eta5-C5H4Y)+ charge transfer transitions. The ferrocenyl compounds undergo cis/trans isomerisation on the OTTLE experiment timescale.
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Reference：
Iron Catalysis in Organic Synthesis | Chemical Reviews,
Iron Catalysis in Organic Synthesis: A Critical Assessment of What It Takes To Make This Base Metal a Multitasking Champion