Synthesis of 1,2,3,4‐Bisiminofullerene and 1,2,3,4‐Bis(triazolino)fullerene—on the Mechanism of the Addition Reactions of Organic Azides to [60]Fullerene

Abstract

Abstract The reactions of organic azides with [60]fullerene have paved the way for the synthesis of adducts with a variety of structures. Treatment of [60]fullerene with 2,2‐dibenzyl‐1,3‐diazidopropane ( 10 ) in refluxing chlorobenzene afforded three products, namely, 8, 9 , and 11 in 18, 25, and 11% yields, respectively. Thermolysis of 9a in refluxing chlorobenzene gave a 40:54:6 mixture of 8, 11 , and C 60 in quantitative yield. No interconversion between 8 and 11 was observed. Whereas 11 was stable towards thermolysis, 8 decomposed to C 60 (35% yield) on refluxing in chlorobenzene for 24 h, but it did not produce any 11 . This indicates that 9a is an intermediate in the formation of 8 and 11 . A general mechanism for the addition of azides to C 60 is proposed. A similar mechanistic pathway is suggested for the thermolysis of 9a .