Abstract
The synthesis of several cyclobutene-functionalized fullerenes was reported. A 1,3-dipolar cycloaddition of C60 with azomethine ylides, generated in situ from 1a-e and formaldehyde, gave the corresponding fuller-1,6-enynes with moderate yields (30-49%). Further heating effected a [2+2] cycloaddition to provide fullerocyclobutenes 3a-d with excellent yields (75-95%). The mechanism of this reaction was confirmed by computational analysis of various reaction pathways, and these studies implicated the strain in the enyne moiety as the driving force for the reaction.
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