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Tenfold Metalation of Ferrocene: Synthesis, Structures, and Metallophilic Interactions in FeC 10 (HgX) 10
Author(s) -
Rupf Susanne Margot,
Schröder Gabriel,
Sievers Robin,
Malischewski Moritz
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202100261
Subject(s) - chemistry , ferrocene , metalation , crystal structure , aqueous solution , medicinal chemistry , trichloroacetic acid , inorganic chemistry , nuclear chemistry , crystallography , organic chemistry , electrochemistry , electrode
The permercuration of ferrocene was achieved by reacting ferrocene with 10 equivalents of mercury(II) butyrate Hg(O 2 CC 3 H 7 ) 2 in a facile one‐pot reaction in multi‐gram scale and high yields. The butyrate groups in FeC 10 (HgX) 10 (X=O 2 CC 3 H 7 ) can be exchanged by treatment with trifluoro‐ or trichloroacetic acid (X=O 2 CCF 3 , O 2 CCCl 3 ). Substitution of the trifluoroacetate groups by halides (X=Cl, F) proceeds easily in aqueous THF. The completeness of metalation was confirmed by NMR and vibrational spectroscopy, mass spectrometry, as well as elemental analysis. Additionally, the first crystal structures of permetallated metallocenes are presented: FeC 10 (HgX) 10 (X=Cl, O 2 CCF 3 , O 2 CCCl 3 ).