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Regioselective synthesis of 1,4-di(organo)[60]fullerenes through DMF-assisted monoaddition of silylmethyl Grignard reagents and subsequent alkylation reaction.

Authors
Type
Published Article
Journal
Journal of the American Chemical Society
0002-7863
Publisher
American Chemical Society
Publication Date
Volume
130
Issue
46
Pages
15429–15436
Identifiers
DOI: 10.1021/ja8041299
PMID: 18950174
Source
Medline

Abstract

Monoaddition of Grignard reagents, in particular tri(organo)silylmethylmagnesium chlorides, to [60]fullerene took place smoothly in the presence of dimethylformamide to produce (organo)(hydro)[60]fullerenes, C60R(1)H, in good yield (up to 93% isolated yield). The hydrofullerene was then deprotonated to generate the corresponding anion, C60R(-), which was then alkylated to obtain 58pi-electron di(organo)[60]fullerenes, C60R(1)R(2), in good to high yield (up to 93% overall yield). The two-step methodology provides a wide variety of 1,4-di(organo)[60] fullerenes bearing the same or different organic addends on the [60] fullerene core. By changing the addends, one can control the chemical and physical properties of the compounds at the molecular and bulk levels.

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