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Preparation of precursors to ferrocenophane ligands
 Škoch, Karel ; Štěpnička, Petr (advisor) ; Veselý, Jan (referee)
Title: Preparation of precursors to ferrocenophane ligands Autor. Karel Škoch Department: Department of Inorganic Chemistry (Faculty of Science, Charles University in Prague) Supervisor: doc. RNDr. Petr Štěpnička, Ph.D. This thesis focuses on a comparison of two alternative literature methods for the preparation [3]ferrocenophan-1-one. One-step Friedel-Crafts acylation of ferrocene with acryloylchloride in presence of aluminium chloride doesn't provide satisfactory yields and the product is contamined with inseparable impurities. For the preparation of a larger amount of pure [3]ferrocenophan-1-one is therefore suggested the original three-step synthesis starting from ferrocenecarbaldehyde. Ferrocenecarbaldehyde is first reacted with malonic acid to give β- ferrocenylacrylic acid, which can be easily reduced with hydrogen to β-ferrocenylpropionic acid. Treatment of β-ferrocenylpropionic acid with trifluoracetic anhydride acid induces heteroannular cyclization, affording [3]ferrocenophan-1-one with good purity and yields (up to 70 % over the three steps). All compounds were characterised by spectroscopic methods (1 H NMR, 13 C NMR and IR).
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