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
|
Download citation |