Reducing ability of supramolecular C60 dianion toward C=O, C=C and N–N bonds

Different from C60 dianion which readily reacts with electrophiles, supramolecular C60 dianion (2) generated from (gamma)-cyclodextrin -bicapped C60(1) and NaBH4(or diborate) in DMSO-H2O (91, v/v) is able to reduce N–N^+, C=C–EWG and C=O bonds to provide the respective dihydro derivatives; 1-mediated reduction of acetophenone with NaBH4 in the presence of (Me2N)2CH2 and EtONa gives turn over frequency (TOF)/h of 400.