Diversion of the Arbuzov reaction: alkylation of C-Cl instead of phosphonic ester formation on the fullerene cage.

We report an "inversed" Arbuzov reaction of the fullerene derivatives CArCl with trialkyl phosphites P(OR) producing alkylated fullerene derivatives CArR (R = Me, Et, iPr, nBu) with almost quantitative yields. This reaction provides a convenient synthetic route for the preparation of a large variety of functionalized fullerene derivatives with tailored properties, e.g.

Synthesis of different types of alkoxy fullerene derivatives from chlorofullerene CCl.

We report novel synthetic routes for facile preparation of highly functionalized fullerene derivatives C(OR)X (X = H, Cl, Br), C(OR)O and C(OR) from chlorofullerene CCl. The first water-soluble fullerene compound bearing residues of 3-oxypropanoic acid demonstrated a potent anti-HIV activity.