Stannabenzenylpotassium: The First Isolable Tin‐Containing Benzene Derivative

• Published in: Chemistry : a European journal Vol. 24; no. 64; pp. 17039 - 17045
• Main Authors: Fujimori, Shiori, Mizuhata, Yoshiyuki, Tokitoh, Norihiro
• Format: Journal Article
• Language: English
• Published: Germany Wiley Subscription Services, Inc 16-11-2018
• Subjects: Anions; Aromatic compounds; aromaticity; Benzene; Chemistry; Crystallography; Germanium; Hydrocarbons; NMR; Nuclear magnetic resonance; phenyl anion; Spectroscopy; stannylene; Tin; X ray spectra; X-ray diffraction; X-ray diffraction; phenyl anion; tin; stannylene; aromaticity
• ISSN: 0947-6539; 1521-3765
• DOI: 10.1002/chem.201804858

In contrast to the well‐investigated sila‐ and germa‐aromatic compounds, very few aromatic compounds containing tin have been reported. Specifically, no stable example of monomeric stannabenzene, that is, the tin analogue of benzene, the simplest aromatic compound, has been isolated until now. In this work, a tin analogue of the phenyl anion, the stannabenzenyl anion, was successfully isolated by utilizing the same strategy as employed for the germanium system. Stannabenzenylpotassium was characterized by X‐ray crystallography, NMR (1H, 13C, and 119Sn) and UV/Vis spectroscopy, together with theoretical calculations.
Two‐faced tin aromatics: The first stable tin‐containing benzene derivative, the stannabenzenyl anion, has been successfully isolated as a monomer both in solution and in the solid state. Its nature, exhibiting aromatic and stannylene features (see figure), was revealed both spectroscopically and structurally and is supported by the results of theoretical calculations.