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.

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