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Alkylation of dihydrofullerenes.

Author
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
Journal
:
The Journal of organic chemistry
Volume
:
67
Issue
:
17
Number of Pages
:
5946-52
Date Published
:
2002
ISSN Number
:
0022-3263
URL
:
https://doi.org/10.1021/jo020216e
DOI
:
10.1021/jo020216e
Short Title
:
J Org Chem
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