Unusual multistep reaction of C70Cl10 with thiols producing C70[SR]5H

Unusual multistep reaction of C70Cl10 with thiols producing C70[SR]5H

[Display omitted] We report a reaction of the chlorofullerene C70Cl10 with thiols producing C70[SR]5H with all organic addends attached around one central pentagon at the pole of the C70 cage. This reaction was shown to proceed via a complicated radical pathway, presumably involving addition, substi...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 57; no. 11; pp. 1215 - 1219
Main Authors: Khakina, Ekaterina A., Peregudov, Alexander S., Yurkova, Anastasiya A., Piven, Natalya P., Shestakov, Alexander F., Troshin, Pavel A.
Format: Journal Article
Language:English
Published: Elsevier Ltd 16-03-2016
Subjects:
DFT calculations
ESR spectroscopy
Fullerenes
Radical reactions
Thiols
Fullerenes
ESR spectroscopy
Thiols
Radical reactions
DFT calculations
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Summary:[Display omitted] We report a reaction of the chlorofullerene C70Cl10 with thiols producing C70[SR]5H with all organic addends attached around one central pentagon at the pole of the C70 cage. This reaction was shown to proceed via a complicated radical pathway, presumably involving addition, substitution, rearrangement, and/or elimination steps. The obtained C70[SR]5H products were shown to be very unstable and undergo quantitative decomposition to pristine C70, RSSR, and RSH at elevated temperatures (e.g., 50°C). Quantum chemical calculations and NMR spectroscopy data showed that cleavage of organic addends from the fullerene cage could be induced by solvation effects in solution.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2016.01.066