Synthesis of a Dihydroxylated Open-Cage [70]Fullerene by a Reductive Ring-Closure Reaction
Yoshifumi Hashikawa1, Yuma Shimizu1, Yasujiro Murata1
1Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan.
Abstract:
Upon heating an open-cage diketo C70 derivative in carbon disulfide, the 1,2-dihydroxylated compound was unprecedentedly formed via a reductive ring-closure reaction. The crystallographic analysis of the diketo derivative revealed a benzenoid character on its orifice which suppresses the nucleophilic addition. The 1,2-dihydroxylated derivative could be transformed into a 1,4-substituted one by an acid-catalyzed reaction. The observed unique reactivity of the diketo derivative is inherently different from those of structurally related C70 isomers as well as a C60 analogue.
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