The poor solubility of certain fullerene derivatives, especially those
bearing several fullerene moieties, has hampered the preparation of n
ew materials. We are proposing a strategy which uses fullerenes bearin
g a readily removable solubilizing group to carry out reaction steps l
eading to a final product with intrinsic low solubility. This is now p
ossible with the one-step conversion of the t-BOC derivative 8a to C-6
0 in over 95% yield. This one-pot conversion involves the in situ form
ation of diene 4 which, after [4 + 2] cycloaddition with dimethyl acet
ylenedicarboxylate, affords the bicyclic adduct 11 undergoing rapid cy
cloreversion to C-60 and dimethyl phthalate. This method was tested wi
th two functionalized C-60 derivatives (14 and 18) as a first step tow
ard the preparation of new nanosized molecular allotropes of carbon an
d rigid fullerene-rich polymers.