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Fullerene with wings

15 May 2014 - Orgo

C70_anthracene_bis-adduct.PNG Neti et al. explain here what happens if you react C70 fullerene with anthracene. The compounds were mixed and heated above the anthracene melting point at 240° for some time, resulting in a neat bis-Diels-Alder adduct (68% yield after column chromatography) with the anthracene units at opposite ends of the cage. The work was a repeat of an identical reaction but then with C60 that was reported 15 years ago by the same group (DOI). As with C60 the reaction is reversible: one unit is lost at 180°C and the other at 220°. As with C60 the anthracene units can be exploited in templated activation of fullerenes and as protective groups.