Synthesis of ferrocenyl derivatives of anthracene

Article abstract of DOI:10.1016/0022-328X(90)85360-B

1-Ferrocenylanthraquinone has been synthesised from the cheap and commercially available 1-diazoniumanthraquinone (Aldrich Fast Red Al salt).Reduction of this anthraquinone with aluminium alkoxide has given good yields of 1-ferrocenyl-anthracene, the first preparation of such polycyclic ferrocenes.The TCNE adduct of the anthracene was prepared in good yield, in marked contrast to the outcome of the redox reaction of ferrocene itself with TCNE.No oxidation was observed with TCNQ.Diels-Alder addition of benzyne resulted in a very low yield (ca. 1 percent)of 1-ferrocentyltriptycene.The 1H and 13C NMR spectra are reported, and discussed in detail together with 57Fe Moessbauer data.