Stereoselective Synthesis of Nontethered trans‐4 Bis(aziridino)[60]fullerene Derivatives†

Abstract

Comprehensive SummaryThe stereoselective preparation of fullerene bis‐adducts through nontethered methods remains difficult due to the significant amount of regioisomers produced. The trans‐4 aziridino[60]fullerenes, C60(NC6H4R)n (n = 1 or 2, R = OMe, OEt, OBu), were selectively synthesized even without a catalyst by reacting octabromofullerene with the corresponding aniline. Nuclear magnetic resonance spectroscopy, UV‐vis spectroscopy, and X‐ray structural analysis provided convincing characterization of the compounds. A possible reaction process was proposed to clarify the synthesis of highly regioselective trans‐4‐bisaziridino[60]fullerenes. The possible application of these aziridino[60]fullerene derivatives as propellant stabilizers was also explored.