Li X, Zhu Y, Shao J, Wang B, Zhang S, Shao Y, Jin X, Yao X, Fang R, Shao X * Lanzhou
University, P. R. of China
Non-Pyrolytic, Large-Scale Synthesis of Trichalcogenasumanene: A Two-Step Approach.
Angew. Chem. Int. Ed. 2014;
53: 535-538
Key words
polycycles - selenium - sulfur - buckybowls
Significance
Sumanenes are nanocarbon buckybowls with a six-membered benzene ring at their center.
The authors report a new synthesis of sulfur- or selenium-substituted sumanenes from
a triphenylene that avoids the very high temperature FVP methods (1000 °C) previously
used. The new method employs much milder conditions and achieves much higher yields
than the only other reported synthesis of trithiosumanene (K. Imamura et al. Chem. Commun. 1999, 1859), and also provides access to the previously unknown triselenasumanene.
Comment
The reported synthesis circumvents the challenge of simultaneous insertion of chalcogens
into the bay positions of triphenylene by first accessing 1,2-dichalcogenin rings.
These six-membered rings presumably have less ring strain than the monochalcogen rings
and can be converted into the desired trichalcogenosumanenes by using copper powder
in a solid-state reaction. This reaction can be performed on multi-gram scale.
