Dihydrofulleroid H{sub 2}C{sub 61}: Synthesis and properties of the parent fulleroid

Journal Article · Wed Aug 26 04:00:00 EDT 1992 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja00044a055· OSTI ID:223959

Suzuki, T; Li, Q; Khemani, K C; Wudl, F ^[1]

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1. Univ. of California, Santa Barbara, CA (United States)

Buckminsterfullerene (C{sub 60}) is conveniently prepared and isolated. Its chemical properties are being investigated with increasing interest. The fulleroids are inflated fullerenes where up to six carbon atoms, each bearing two substituents, are added systematically to C{sub 60}. In this communication we report the preparation of the simplest, {open_quotes}parent{close_quotes} fulleroid formed by the reaction of fullerene C{sub 60} with diazomethane. Diazomethane reacts with (C{sub 60}) to give a thermally unstable compound, (CH{sub 2}N{sub 2})(C{sub 60}) in 44% yield. It was shown that in fulleroid synthese, the intermediate pyrazoline can be isolated and characterized; the first step of fulleroid synthesis is a dipolar addition across the reactive 6-ring-6-ring (pyracyclene) junction; thermal nitrogen loss occurs concomitantly with rearrangement; and comparative {sup 1}H NMR with a known bicyclic hydrocarbon incapable of sustaining an extended ring current indicates that there are no extended ring currents in the fulleroid {open_quotes}(pi){close_quotes} system. 16 refs., 1 fig.

• Sponsoring Organization: USDOE
• OSTI ID: 223959
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 18 Vol. 114; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

40 CHEMISTRY
CHEMICAL PROPERTIES
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
FULLERENES