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Issue 30, 2019
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Diversion of the Arbuzov reaction: alkylation of C–Cl instead of phosphonic ester formation on the fullerene cage

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Abstract

We report an “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 the preparation of a large 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.

Graphical abstract: Diversion of the Arbuzov reaction: alkylation of C–Cl instead of phosphonic ester formation on the fullerene cage

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Article information


Submitted
12 Mar 2019
Accepted
17 May 2019
First published
17 May 2019

Org. Biomol. Chem., 2019,17, 7155-7160
Article type
Paper

Diversion of the Arbuzov reaction: alkylation of C–Cl instead of phosphonic ester formation on the fullerene cage

O. A. Kraevaya, A. S. Peregudov, S. I. Troyanov, I. Godovikov, N. E. Fedorova, R. R. Klimova, V. A. Sergeeva, L. V. Kameneva, E. S. Ershova, V. M. Martynenko, S. Claes, A. A. Kushch, S. V. Kostyuk, D. Schols, A. F. Shestakov and P. A. Troshin, Org. Biomol. Chem., 2019, 17, 7155
DOI: 10.1039/C9OB00593E

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