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

Organic & Biomolecular Chemistry
Bolong ZhangWallace W H Wong

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.

References

Feb 14, 2006·The Journal of Organic Chemistry·Zhiguo ZhouStephen R Wilson
Mar 4, 2011·Journal of Computational Chemistry·Stefan GrimmeLars Goerigk
Mar 29, 2011·The Journal of Physical Chemistry. a·Sílvia OsunaMiquel Solà
Dec 3, 2014·Physical Chemistry Chemical Physics : PCCP·Jean-Claude BrodovitchPaul W Percival
May 20, 2015·Journal of the American Chemical Society·Maira R CerónLuis Echegoyen
May 21, 2015·Chemical Communications : Chem Comm·Bolong ZhangWallace W H Wong

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Citations

Oct 16, 2015·Journal of the American Chemical Society·Tiezheng JiaPatrick J Walsh
Jun 25, 2016·Beilstein Journal of Organic Chemistry·Bolong ZhangWallace Wing Ho Wong

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