KCS

Single electron transfer (SET)-promoted photochemical reactions of C₆₀ fullerene with alpha-silyl tertiary amines to prepare alpha-aminofullerenes were carried out and their reaction mechanisms were explored. The results showed that photoirradiation of 10% EtOH-toluene solutions containing amine donors and C₆₀ fullerene gave rise to formation of alpha-aminofullerenes with modest to high chemical yields. The feasible mechanistic pathways of photoaddition reactions of alpha-silyl tertiary amines with C₆₀ leading to the formation of alpha-aminofullerenes described above would begin formation of aminium radical and fullerene anion intermediates arising by SET from alpha-silyl tertiary amines to triplet excited state of C₆₀. Then, EtOH-assisted desilylation from aminium radicals occurs to produce alpha-amino radicals, which form C-C bond with fullerene anion. Finally, subsequent protonation leads to the formation of α-aminofullerenes.