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Chlorination-Promoted Skeletal Transformation of IPR C76 Discovered via Trifluoromethylation under Formation of non-IPR C76(CF3)nFm

Nadezhda B. Tamm,  Victor A. Brotsman,  Vitaliy Yu. Markov,  Erhard Kemnitz  and  Sergey I. Troyanov 

Abstract

High-temperature chlorination of Isolated-Pentagon Rule (IPR) D2-C76 fullerene followed by high-temperature trifluoromethylation of non-IPR C76 chlorides with CF3I unexpectedly resulted in a series of non-IPR C76(CF3)nFm compounds. Their separation by means of HPLC followed by single crystal X-ray diffraction study with the use of synchrotron radiation revealed the mixed CF3/F structures of non-classical (NC), non-IPR C76(NC2)(CF3)14, C76(NC2)(CF3)14F2, and C76(NC2)(CF3)16F6, all containing two heptagons, three pairs of fused pentagons, and two triples of sequentially fused pentagons in the carbon cages. The possible pathway from D2-C76 to IPR-violating C76(NC2) cage is suggested on the basis of a topological analysis.

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Publication details

The article was received on 14 Mar 2018, accepted on 16 Apr 2018 and first published on 16 Apr 2018


Article type: Communication
DOI: 10.1039/C8DT00984H
Citation: Dalton Trans., 2018, Accepted Manuscript
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    Chlorination-Promoted Skeletal Transformation of IPR C76 Discovered via Trifluoromethylation under Formation of non-IPR C76(CF3)nFm

    N. B. Tamm, V. A. Brotsman, V. Yu. Markov, E. Kemnitz and S. I. Troyanov, Dalton Trans., 2018, Accepted Manuscript , DOI: 10.1039/C8DT00984H

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