Photoaddition reactions of C₆₀ with tertiary N-arylmethyl-N-trimethylsilylmethyl substituted α-aminonitriles were explored. The results show that these photoreactions produce both trimethylsilyl- and cyano group containing fulleropyrrolidines as major products through pathways involving 1,3-dipolar cycloaddition of azomethine ylide intermediates. The ylides are formed either by SET from α-aminonitriles to the triplet excited state of C₆₀ (in N₂-purged solutions) followed by desilylation or deprotonation, or by hydrogen atom abstraction by singlet oxygen (in O₂-purged solutions). In contrast, photoreactions of C₆₀ with analogous amines that do not contain trimethylsilyl group form fulleropyrrolidines that contain aryl- and cyano substitutents on the pyrrolidine ring. The efficiencies of these photoaddition reactions are influenced by several factors including reaction condition (N₂ or O₂-purged), solvent polarity, the electronic and structural nature of α-aminonitriles and additive. The presence of trimethylsilyl group in the α-aminonitrile substrates plays a crucial role in enhancing the efficiencies of the fulleropyrrolidine forming reactions.

研究了C ₆₀与N-芳基甲基-N-三甲基甲硅烷基甲基取代的α-氨基腈的光加成反应。结果表明，这些光反应通过涉及偶氮甲碱内酯中间体的1，3-偶极环加成的途径，产生了含有三甲基甲硅烷基和氰基的全吡咯烷酮作为主要产物。通过SET从α-氨基腈到C ₆₀的三重态激发态（在N ₂净化溶液中），然后进行甲硅烷基化或去质子化，或通过单线态氧夺取氢原子（在O ₂净化溶液中）形成酰基化物。相反，C _60的光反应与不含三甲基甲硅烷基的类似胺形成的全吡咯烷酮在吡咯烷环上含有芳基和氰基取代基。这些光加成反应的效率受几个因素影响，包括反应条件（N ₂或O ₂净化），溶剂极性，α-氨基腈和添加剂的电子和结构性质。α-氨基腈底物中三甲基甲硅烷基的存在在增强全吡咯烷形成反应的效率中起着至关重要的作用。