Issue 42, 2015

Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

Abstract

The regioselective synthesis of fullerene multiadducts was achieved from commercially available reagents in one pot over two steps. The configuration of the isolated regioisomers was determined using various NMR methods, UV-vis spectroscopy and electrochemical analysis with the structure of one isomer confirmed by single crystal X-ray analysis. Interesting variation in regioselectivity was observed when different amino acid reagents were used in the reactions. Theoretical calculations and additional experiments, such as deuterium exchange, led to a proposed mechanism for the regioselective product formation.

Graphical abstract: Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

Supplementary files

Article information

Article type
Paper
Submitted
05 Aug 2015
Accepted
28 Aug 2015
First published
04 Sep 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 10505-10510

Author version available

Regioselective synthesis of fullerene multiadducts via tether-directed 1,3-dipolar cycloaddition

B. Zhang, J. M. White, D. J. Jones and W. W. H. Wong, Org. Biomol. Chem., 2015, 13, 10505 DOI: 10.1039/C5OB01630D

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