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Functionalization of C60 by Cycloaddition Reactions

Published online by Cambridge University Press:  15 February 2011

Stephen R. Wilson,
Jingrong Cao,
Qingyi Lug,
Yunhui Wu,
Nikolaos Kaprinidas,
George Lem,
Martin Saunders,
Hugo A. Jimenez-Vasquez and
David I. Schuster
Stephen R. Wilson
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
Jingrong Cao
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
Qingyi Lug
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
Yunhui Wu
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
Nikolaos Kaprinidas
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
George Lem
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
Martin Saunders
Affiliation:
Department of Chemistry, Yale University, New Haven, CT 06520
Hugo A. Jimenez-Vasquez
Affiliation:
Department of Chemistry, Yale University, New Haven, CT 06520
David I. Schuster
Affiliation:
Department of Chemistry, New York University, New York, NY 10003
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Abstract

Functionalization of C60 has been achieved by [2+2] photocycloaddition reactions of enones and [2+4] cycloaddition reactions of dienes, the course of these reactions can be followed using electrospray mass spectrometry using a special tagging reagent. Using tagged C60 it was shown that cis and trans cycloadducts are formed from ketones such as 3-methylcyclohexenone. We have also employed the new technique of 3He NMR spectrometry. 3He is an NMR-active nucleus. Fullerenes containing an endohedral 3He atom can be examined by NMR to obtain structural information and potentially determine isomer distributions. Examples, of helium spectra of fullerene hydrides are presented.

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References

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