Exploiting thiacalix4arene and sulfur‐bridged bisphenolates as ligands for bioinorganic studies involving iron(III) requires the prior development of synthetic routes (varying substituents and reaction conditions) to construct complexes with low nuclearities and accessible coordination sites, which was in the focus of this investigation. Treating p‐tert‐butylthiacalix4arene (H₄TC) and 1, 4‐dimethyl‐p‐tert‐butylthiacalix4arene (Me₂H₂TC) with Fe[N(SiMe₃)₂]₃ yielded in the formation of the iron(III) complexes [(Me₃SiTC)₂Fe₂] (1) and [(Me₂TC)₃Fe₂] (3), respectively. While 1 is a sandwich compound, in 3 one [Me₂TC]^2– unit is bridging two [Me₂TCFe]⁺ moieties. Employing thiobisphenolates as ligands it turned out, that in dependence on the residues R and the preparation method it is possible to selectively access sandwich, anionic or neutral complexes, which were shown to contain central high‐spin iron(III) atoms. The syntheses, structures, and electronic properties of three iron(III) bisphenolate complexes, [^ClL₂Fe]NEt₃H (4), [^MeLFeCl₂]NEt₃H (5), and [^tBuLFeCl(thf)] (7) are discussed.

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