SYNTHESIS OF 1,2,3,4-BISIMINOFULLERENE AND 1,2,3,4-BIS(TRIAZOLINO) FULLERENE - ON THE MECHANISM OF THE ADDITION-REACTIONS OF ORGANIC AZIDESTO [60]FULLERENE

The reactions of organic azides with [60]fullerene have paved the way for the synthesis of adducts with a variety of structures. Treatment o f[60]fullerene with 2,7-dibenzyl-1,3-diazidopropane (10) in refluxing chlorobenzene afforded three products, namely, 5, 9, and 11 in IS, 25, and ii % yields, respectively. Thermolysis of 9a in refluxing chlorob enzene 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 sta ble towards thermolysis, 8 decomposed to C-60 (35% yield) on refluxing in chlorobenzene for 24 h, but it did not produce any PI, This indica tes 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 m echanistic pathway is suggested for the thermolysis of 9a.