Toward an understanding of the mechanism of the Arbuzov-type reaction of C60Cl6with phosphites

Ekaterina A. Khakina, Olga R. Yamilova, Artyom V. Novikov, Ivan A. Godovikov, Alexander S. Peregudov, Pavel A. Troshin

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8 Citations (Scopus)

Abstract

UV–VIS spectroscopy, ESR spectroscopy, HPLC, and mass spectrometry were applied to an investigation of the Arbuzov-type reaction of the chlorofullerene C60Cl6with trialkyl phosphites (P(OR)3). It was shown that this reaction proceeds via a complicated radical pathway involving single electron transfer from phosphite to the fullerene cage. The reaction rate constant of 2.9 × 10−2 s−1was estimated from the dynamic UV–VIS measurements. A family of new compounds, C60[P(O)(OMe)2]5H, C60[P(O)(OR)2]4ArH (R = Me, Et; Ar = C6H3Cl2, C6H4CH3), C60[P(O)(OEt)2]H, C60[P(O)(OBu)2]3H, were isolated and characterized.

Original languageEnglish
Pages (from-to)5570-5574
Number of pages5
JournalTetrahedron Letters
Volume57
Issue number50
DOIs
Publication statusPublished - 2016

Keywords

  • Arbuzov-type reaction
  • ESR spectroscopy
  • Fullerenes
  • Phosphites
  • Radical reaction

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