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[2 + 2] Cycloaddition Reaction to Sc3N@Ih-C80. The Formation of Very Stable [5,6]- and [6,6]-Adducts

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posted on 09.02.2011, 00:00 by Fang-Fang Li, Julio R. Pinzón, Brandon Q. Mercado, Marilyn M. Olmstead, Alan L. Balch, Luis Echegoyen
The [2 + 2] cycloaddition reaction of Sc3N@Ih-C80 with benzyne was successfully conducted for the first time. The reaction affords both the [5,6]- and [6,6]-monoadducts with a four-membered ring attached to the cage surface on 5,6- and 6,6-ring fusions, respectively. The compounds were characterized by MALDI-TOF, NMR, UV−vis−NIR spectroscopy and single-crystal X-ray structure determination. The electrochemical behavior of both monoadducts was investigated. The [5,6]-regioisomer displays reversible cathodic behavior similar to that observed for the fulleropyrrolidines with a 5,6-addition pattern. Surprisingly, the [6,6]-regioisomer also exhibits reversible cathodic behavior. The interconversion reaction of the isomers was also explored, and the results showed that both monoadducts are thermally very stable.

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