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Synfacts 2006(6): 0567-0567  
DOI: 10.1055/s-2006-934512
Synthesis of Materials and Unnatural Products
© Georg Thieme Verlag Stuttgart · New York

Fullerobutenes

Contributor(s): Timothy Swager, Scott Meek
N. Martín*, M. Altable, S. Filippone, A. Martín-Domenech, M. Güell, M. Solá
Universidad Complutense de Madrid, Universidad de Girona, Spain
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Publication History

Publication Date:
19 May 2006 (online)

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Significance

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.