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Diversion of the Arbuzov Reaction: Alkylation of C-Cl Instead of Phosphonic Ester Formation on the Fullerene Cage

Abstract

We report “inversed” Arbuzov reaction of the fullerene derivatives C60Ar5Cl with trialkyl phosphites P(OR)3 producing alkylated fullerene derivatives C60Ar5R (R=Me, Et, iPr, nBu) with almost quantitative yields. This reaction provides a convenient synthetic route for preparation of a big variety of functionalized fullerene derivatives with tailored properties, e.g. water-soluble compounds demonstrating promising antiviral activities against HCMV, HSV1, HIV and several influenza virus strains.

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Publication details

The article was received on 12 Mar 2019, accepted on 17 May 2019 and first published on 17 May 2019


Article type: Paper
DOI: 10.1039/C9OB00593E
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Diversion of the Arbuzov Reaction: Alkylation of C-Cl Instead of Phosphonic Ester Formation on the Fullerene Cage

    O. Kraevaya, A. S. Peregudov, S. I. Troyanov, I. Godovikov, N. E. Fedorova, R. R. Klimova, V. Sergeeva, L. V. Kameneva, E. Ershova, V. M. Martynenko, S. Claes, A. A. Kushch, S. Kostyuk, D. Schols, A. F. Shestakov and P. Troshin, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB00593E

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