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

Ekaterina A. Khakina, Alexander S. Peregudov, Anastasiya A. Yurkova, Natalya P. Piven, Alexander F. Shestakov, Pavel A. Troshin

Research output: Contribution to journalArticlepeer-review

11 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)1215-1219
Number of pages5
JournalTetrahedron Letters
Volume57
Issue number11
DOIs
Publication statusPublished - 16 Mar 2016
Externally publishedYes

Keywords

  • DFT calculations
  • ESR spectroscopy
  • Fullerenes
  • Radical reactions
  • Thiols

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