Synfacts 2019; 15(11): 1256
DOI: 10.1055/s-0039-1691058
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Sumanene

Timothy M. Swager
Jie Li
Sakurai H. * Daiko T, Hirao T. * Osaka University, Japan
A Synthesis of Sumanene, a Fullerene Fragment.

Science 2003;
301: 1878-1878
Further Information

Publication History

Publication Date:
18 October 2019 (online)



As model compounds of fullerenes as well as possible synthetic intermediates for artificially designed fullerene derivatives, bowl-shaped π-conjugated compounds become important. A key partial C 3v -symmetric structure of fullerenes, sumanene, is synthesized in this paper. Sumanene has advantages that allow it to undergo further functionalization to create new bowl-shaped molecules. The authors report a synthetic method that enables access to sumanene under mild conditions in a short series of steps that start from commercially available norbornadiene.



In this paper, the authors present an efficient strategy to synthesize sumanene. Instead of starting from the planar compounds, the authors constructed the three-dimensional framework by using tetrahedral sp3 carbon units. Two procedures were tried to achieve the trimerization of norbornadiene, and the stepwise transmetalation via an organotin compound increased the overall yield of syn-2 from 2% to 11%. In contrast to the other well-studied bowl-shaped compound corannulene, sumanene is shown to be very rigid and the bowl-to-bowl inversion only occurs at high temperature.