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Mesobiliverdin IXalpha dimethyl ester (7) was obtained by hydrogenation of protobiliverdin IXalpha dimethyl ester (8).Zinc 5-oxamesoporphyrin IX dimethyl ester tetrafluoroborate (6) was prepared by the cyclization of 7 with zinc acetate in acetic anhydride followed by a treatment with aqueous sodium tetrafluoroborate.Bis(pyridine) mesoverdohemochrome IXalpha dimethyl ester (4) was obtained by the cyclization of 7 with both iron(II) sulfate and iron(III) chloride in acetic anhydride containing a small amount of pyridine.Bis(tosylmethyl isocyanide)mesoverdohemochrome IXalpha dimethyl ester (5) was prepared by the addition of excess tosylmethyl isocyanide (TsCH2NC) to 4.Both 4 and 5 reacted with ammonia to give iron(III) 5-azamesoporphyrin IX dimethyl ester (10).The Moessbauer spectra of bis(pyridine) verdohemochromes (4, 13, and 14) showed doublet peaks having parameters of delta=0.41-0.43 mm s-1 and DeltaEQ=1.24-1.26 mm s-1, indicating that the oxidation states of the central irons of these complexes are iron(II).Bis(TsCH2NC) verdohemochromes (5,15, and 17) showed single peaks having parameters of delta=0.21-0.28 mm s-1.Unstable intermediate and stable final bis(TsCH2NC) octaethyl verdohemochromes, obtained by the addition of TsCH2NC to 4, were compared with the 1H NMR and Moessbauer spectra.
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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