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 C60Ar5Cl with trialkyl phosphites P(OR)3 producing alkylated fullerene derivatives C60Ar5R (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. water-soluble compounds demonstrating promising antiviral activities against HCMV, HSV1, HIV and several influenza virus strains.

Synthesis of different types of alkoxy fullerene derivatives from chlorofullerene C60Cl6.

We report novel synthetic routes for facile preparation of highly functionalized fullerene derivatives C60(OR)5X (X = H, Cl, Br), C60(OR)4O and C60(OR)2 from chlorofullerene C60Cl6. The first water-soluble fullerene compound bearing residues of 3-oxypropanoic acid demonstrated a potent anti-HIV activity.