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Diversion of the Arbuzov reaction: alkylation of C–Cl instead of phosphonic ester formation on the fullerene cage†
Alexander S. Peregudov,Sergey I. Troyanov,Ivan Godovikov,Natalya E. Fedorova,Regina R. Klimova,Vasilina A. Sergeeva,Larisa V. Kameneva,Elizaveta S. Ershova,Vyacheslav M. Martynenko,Sandra Claes,Alla A. Kushch,Svetlana V. Kostyuk,Dominique Schols
Organic & Biomolecular Chemistry Pub Date : 05/17/2019 00:00:00 , DOI:10.1039/C9OB00593E
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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