Isolation and characterization of unsymmetrical C(60)Me(5)O(3)H, a cage-opened bisepoxide ketone: tautomerism involving a fullerene cage bond.
Bisepoxide ketone C(60)Me(5)O(3)H, possessing a nine-membered hole in the cage, has been isolated from the reaction of C(60)Cl(6) with methyllithium followed by hydrolysis. It is a tautomer of the recently isolated bisepoxide fullerenol, this tautomerism being the first example involving a cage C-C bond, and may be driven by cage strain. Like the fullerenol, the ketone gives a high C(58)(+) fragmentation ion intensity during EI mass spectrometry.
Al-Matar
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The Chemistry Laboratory, CPES School, University of Sussex, Brighton BN1 9QJ, U.K.
Abdul-Sada
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Avent
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Taylor
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