ISSN:
0947-6539
Keywords:
azide adducts
;
fullerenes
;
reaction mechanisms
;
regioselectivity
;
thermolysis
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
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 C60 in quantitative yield. No interconversion between 8 and 11 was observed. Whereas 11 was stable towards thermolysis, 8 decomposed to C60 (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 C60 is proposed. A similar mechanistic pathway is suggested for the thermolysis of 9a.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970030514
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