Isolation of Two Seven-Membered Ring C58 Fullerene Derivatives: C58F17CF3 and C58F18

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Science  08 Jul 2005:
Vol. 309, Issue 5732, pp. 278-281
DOI: 10.1126/science.1111904

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Fluorination of C60 at 550°C leads to milligram quantities of two stable fullerene derivatives with 58-carbon cage structures: C58F18 and C58F17CF3. The compounds were characterized by mass spectrometry and fluorine nuclear magnetic resonance spectroscopy, and the data support a heptagonal ring in the framework. The resulting strain, which has hindered past attempts to prepare these smaller quasi-fullerenes, is mitigated here by hybridization change of some of the carbons in the pentagons from sp2 to sp3 because of fluorine addition. The loss of carbon from C60 is believed to occur via sequential fluorine addition to a C–C single bond and an adjacent C[dbond]C bond, followed by loss of a :CF2 carbene.

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