Fullerene with wings

15 May 2014 - Orgo

C70 anthracene bis adduct.PNGNeti 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.