J. Averdung et al., PHOTOREACTIONS WITH C60-FULLERENE - [3-DIPHENYL-2H-AZIRINE(2] PHOTOCYCLOADDITION OF 2,3), Chemische Berichte, 127(4), 1994, pp. 787-789
Upon irradiation 2,3-Diphenyl-2H-azirine (2) is added to C60 1 with fo
rmation of mono and oligo adducts. -(3,4-Dihy-dro-2,5-diphenyl-2H-pyrr
olo)fulleren-60 (3) has been isolated and identified by standard spect
roscopic methods. Mechanistic studies revealed two reaction paths lead
ing to 3, i.e. the classic 1,3-dipolar cycloaddition via the nitrile y
lide 4 (direct irradiation) or a route via 2-azaallenyl radical cation
s 5 (sensitization by photoinduced electron transfer).