Alkylation of dihydrofullerenes.
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Abstract | :
The fulleride dianions C(60)(2-) and C(70)(2-) were generated by deprotonation of the corresponding hydrogenated fullerenes, 1,2-C(60)H(2) and 1,2-C(70)H(2). These anions were prepared in the presence of a variety of alkylating agents, and mono- or dialkylated products were obtained. Alkylation was not successful with sulfonate ester alkylating agents. Deprotonation of monoalkylated compounds, followed by second alkylation with a different alkylating agent, produced heterodialkylated compounds. The monoalkyated material was invariably the 1,2-isomers, while the dialkylated materials were generally 1,4-isomers, although some 1,2-isomer was observed in the C(70) context. The major product from alkylation of C(70)(2-) was the 7,23-isomer 13a, a structure where the alkylation took place near the equator of the fullerene cage, rather than at the more strained carbons near the poles. |
Year of Publication | :
2002
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Journal | :
The Journal of organic chemistry
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Volume | :
67
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Issue | :
17
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Number of Pages | :
5946-52
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Date Published | :
2002
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ISSN Number | :
0022-3263
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URL | :
https://doi.org/10.1021/jo020216e
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DOI | :
10.1021/jo020216e
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Short Title | :
J Org Chem
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