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Addition of Azomethine Ylides: Fulleropyrrolidines

  • Chapter
Fullerenes: From Synthesis to Optoelectronic Properties

Part of the book series: Developments in Fullerene Science ((DFUL,volume 4))

Abstract

Although extensively studied in the last decade, the fullerenes continue to be a most exciting and promising challenge in current chemical research. After a first phase characterized by theoretical, physical and physicochemical studies, a well established “organic chemistry of the fullerenes” developed in a very rapid progression to the point that, currently, a wide variety of functionalized fullerenes are available through simple and accessible synthetic routes [1,2]. Among the many reactions that were successfully developed, the 1,3-dipolar cycloaddition of azomethine ylides provides a valuable synthetic procedure for the preparation of functionalized fullerenes [3–5]. The product of the reaction, named fulleropyrrolidine because a pyrrolidine ring is fused to a ring-junction of a fullerene, retains the basic properties of the parent fullerene and can be used as a starting material for further functionalization. Whereas monofunctionalization of the highly symmetrical [60]fullerene affords a single fulleropyrrolidine, the same addition to [70]fullerene [6, 7] gives rise to mixtures of regioisomers. For this reason, current fulleropyrrolidine syntheses are predominantly carried out using [60]fullerene.

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  1. Organic Chemistry Department, University of Padova, Via Marzolo, 1, 35131, Padova, Italy

    Michele Maggini & Enzo Menna

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  1. Michele Maggini
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  2. Enzo Menna
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  1. Radiation Laboratory, Notre Dame University, Indiana, USA

    Dirk M. Guldi

  2. Department of Organic Chemistry, University Complutense of Madrid, Spain

    Nazario Martin

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Maggini, M., Menna, E. (2002). Addition of Azomethine Ylides: Fulleropyrrolidines. In: Guldi, D.M., Martin, N. (eds) Fullerenes: From Synthesis to Optoelectronic Properties. Developments in Fullerene Science, vol 4. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9902-3_1

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