[2 + 2] Cycloaddition Reaction to Sc3N@Ih-C80. The Formation of Very Stable [5,6]- and [6,6]-Adducts
- 10 January 2011
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 133 (5), 1563-1571
- https://doi.org/10.1021/ja1097176
Abstract
The [2 + 2] cycloaddition reaction of Sc(3)N@I(h)-C(80) 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.Keywords
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