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Germabenzenylpotassium: A Germanium Analogue of a Phenyl Anion
Author(s) -
Mizuhata Yoshiyuki,
Fujimori Shiori,
Sasamori Takahiro,
Tokitoh Norihiro
Publication year - 2017
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201700801
Subject(s) - germanium , chemistry , trimethylsilyl , moiety , aryl , ion , crystallography , monomer , tris , molecule , crystal structure , inert gas , medicinal chemistry , stereochemistry , organic chemistry , silicon , polymer , alkyl , biochemistry
Reduction of the stable germabenzene, 1‐Tbt‐2‐ tert ‐butyl‐germabenzene (Tbt=2,4,6‐tris[bis(trimethylsilyl)methyl]phenyl), with KC 8 resulted in the formation of 2‐ tert ‐butylgermabenzenylpotassium, that is, the germanium analogue of phenylpotassium, under concomitant elimination of the aryl group from the Ge atom. Under an inert atmosphere, this germabenzenylpotassium could be isolated in the form of stable yellow crystals. In the crystalline state, as well as in solution, the germabenzenyl moiety adopts a monomeric form, even though the X‐ray diffraction analysis suggests the presence of highly reactive Ge=C double bonds. The spectroscopic and X‐ray crystallographic analyses, in combination with theoretical calculations indicate an ambident character for this germabenzenyl anion, with contributions from aromatic and germylene resonance structures.