Abstract
Photochemical [2 + 2] cycloaddition of C60 with N,N-diethyl-4-methyl-3-penten-1-yn-1-amine (1) afforded the stable C60-fused cyclobutenamine 2 which underwent self-sensitized photooxidation to dihydrofullerenone amide 4 in high yield. Fullerenes C60 and C70 react thermally with tetraalkoxyethylenes to give dihydrofullerene cyclobutanediketals, which undergo a clean cycloreversion to fullerenes on irradiation with visible or UV light. Attempted hydrolysis of the ketals was unsuccessful, but treatment of 1,2-(6161,62,62-tetraethoxycyclobutano)dihydro[60]fullerene (8) with TMSI gave ring-contracted product 11 (by cleavage of the C−C bond to the fullerene fragment) along with reduction product 12.
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