Fragmentation of the [60]fullerene cage during bromination

Heating [60]fullerene with Br2/FeCl3/benzene under reflux for 24 h yields in addition to the previously observed phenylated fullerenes, two bromine-containing open-cage products of 768/770 and 848 amu, each of which fragments to decacyclene during EI mass spectrometry. This provides an example of the reverse of the [60]fullerene synthesis from aromatic precursors.