Addition of azomethine ylides to C[sub 60]. Synthesis, characterization, and functionalization of fullerene pyrrolidines

Journal Article · Wed Oct 20 00:00:00 EDT 1993 · Journal of the American Chemical Society; (United States)

DOI:https://doi.org/10.1021/ja00074a056· OSTI ID:5116185

Maggini, M; Scorrano, G ^[1]; Prato, M ^[2]

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1. Centro Meccanismi di Reazioni Organiche del CNR, Padova (Italy)
2. Universita di Trieste (Italy)

We report herein a new and very general fullerene functionalization, based on the 1,3-dipolar cycloaddition of azomethine ylides to C[sub 60]. Azomethine ylides, planar species of general formula (R[sup 1]R[sup 2])-C=N[sup +](R[sup 3]) - C[sup [minus]](R[sup 4]R[sup 5]), represent one of the most reactive and versatile classes of 1,3-dipoles. They can be generated from a wide variety of easily accessible starting materials and react readily with a range of dipolarophiles. The products of cycloaddition, substituted pyrrolidines, are well suited for further functionalization. A very easy way of generating azomethine ylides is the [open quotes]decarboxylation route.[close quotes] Another approach to azomethine ylides, the thermal ring-opening of aziridines, gave the same profitable results. The present new fullerene functionalization offers high potential in the materials chemistry field. Of the several uses that can be envisioned, two representative examples are reported. 17 refs., 1 fig.

• OSTI ID: 5116185
• Journal Information: Journal of the American Chemical Society; (United States), Vol. 115:21; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC
ORGANIC
PHYSICAL AND ANALYTICAL CHEMISTRY
FULLERENES
CHEMICAL REACTIONS
DERIVATIZATION
ORGANIC COMPOUNDS
NUCLEAR MAGNETIC RESONANCE
VOLTAMETRY
CARBON
ELEMENTS
MAGNETIC RESONANCE
NONMETALS
RESONANCE
400201* - Chemical & Physicochemical Properties
400102 - Chemical & Spectral Procedures