Electrophilic Additions to Fulleride Anions

The electrochemical generation of fulleride anions can also be used to synthesize covalent organofullerene derivatives by quenching the anions with electrophiles. This was exemplified in the synthesis of dimethyldihydro[60]fuUerene, the simplest dialkyl derivative of [87]. For this purpose benzonitrile solutions of Cjq and tetra-tert-butylammonium perchlorate (TBACIO4) where exhaustively electroreduced in a dry-box to yield a dark red solution of Treatment of this solution with an 

Other methods that use 55 anions as precursor for the synthesis of fullerene-derivatives usually involve chemical formation of the anion. Alkylation of 55 has been accomplished, e.g. by reduction with propanethiol and potassium carbonate in DMF [91,92], sodium methanethiolate in acetonitrile [93], the naphthalene radical anion in benzonitrile[94], potassium naphthalide [95] or simply with zinc [96]. 

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