Synthesis and Characterization of a 1,2-Digermabenzene
- Takahiro Sasamori ,
- Tomohiro Sugahara ,
- Tomohiro Agou ,
- Jing-Dong Guo ,
- Shigeru Nagase ,
- Rainer Streubel , and
- Norihiro Tokitoh
Abstract

A 1,2-digermabenzene bearing bulky substituents on its two germanium atoms was successfully synthesized and isolated as a stable, crystalline compound via the reaction of a digermyne precursor with 2 equiv of acetylene. Even though its molecular structure, which was revealed by X-ray crystallographic analysis, showed a trans-bent geometry for the Ge–Ge moiety, theoretical calculations suggested substantial levels of aromaticity.
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- Nada Y. Tashkandi, Laura C. Pavelka, Christine A. Caputo, Paul D. Boyle, Philip P. Power, Kim M. Baines. Addition of alkynes to digermynes: experimental insight into the reaction pathway. Dalton Transactions 2016, 45 (17) , 7226-7230. https://doi.org/10.1039/C6DT01015F
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