Syntheses of aziridino-[60]fullerenes via photochemically induced conversions of 1,2,3-triazolino-[60]fullerenes and azafulleroids

Averdung J, Mattay J. Syntheses of aziridino-[60]fullerenes via photochemically induced conversions of 1,2,3-triazolino-[60]fullerenes and azafulleroids. JOURNAL OF INFORMATION RECORDING. 1996;22(5-6):577-580.The reaction of C-60 with aryl azides 1 in dichlorobenzene at room temperature leads to isolable triazolinofullerene derivatives 2a and 2b. Photolysis of 2 selectively yields the aziridinofullerenes 4. In contrast to the photolysis the thermolysis affords the azafulleroids 3 as main product next to C-60. In addition the first photochemcially induced rearrangement of azafulleroids (1,6-aza-bridged isomers) to aziridinofullerenes (1,2-aza-bridged isomers) is described. Beside aziridines 4 the photochemical reactions of azides 1 with C-60 predominantly yield one novel C-s symmetrical bisadduct, respectively