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Issue 25, 2020
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Electrochemical regioselective alkylations of a [60]fulleroindoline with bulky alkyl bromides

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Abstract

Electrochemical alkylations of a [60]fulleroindoline with different bulky alkyl bromides exhibit different reaction behaviors. The hydroalkylation and dialkylation of the electrochemically generated dianionic [60]fulleroindoline with bulky 2,4,6-tris(bromomethyl)mesitylene give rise to 1,2,3,16-adducts. In comparison, the hydroalkylation of the dianionic [60]fulleroindoline with bulkier diphenylbromomethane still affords a 1,2,3,16-adduct, while the corresponding dialkylation provides a sterically favoured 1,4,9,12-adduct, which is scarcely investigated, as the major product along with the isomeric 1,2,3,16-adduct as the minor product. The structures of these products have been determined by spectroscopic data and single-crystal X-ray diffraction analysis. A plausible reaction mechanism has been proposed to explain the formation of the observed products.

Graphical abstract: Electrochemical regioselective alkylations of a [60]fulleroindoline with bulky alkyl bromides

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Supplementary files

Article information


Submitted
27 Apr 2020
Accepted
02 Jun 2020
First published
02 Jun 2020

Org. Biomol. Chem., 2020,18, 4783-4787
Article type
Paper

Electrochemical regioselective alkylations of a [60]fulleroindoline with bulky alkyl bromides

Y. Yang, C. Niu, M. Chen, S. Yang and G. Wang, Org. Biomol. Chem., 2020, 18, 4783
DOI: 10.1039/D0OB00876A

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