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

Autor: Kraevaya OA; Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russia. troshin2003@inbox.ru and IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia., Peregudov AS; INEOS RAS, Vavylova St. 28, B-334, Moscow, 119991, Russia., Troyanov SI; Department of Chemistry, Moscow Lomonosov State University, Leninskie gory, Moscow, 119991, Russia., Godovikov I; INEOS RAS, Vavylova St. 28, B-334, Moscow, 119991, Russia., Fedorova NE; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia., Klimova RR; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia., Sergeeva VA; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia., Kameneva LV; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia., Ershova ES; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia., Martynenko VM; IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia., Claes S; Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven, Belgium., Kushch AA; Honored Academician N.F.Gamaleya National Research Centre for Epidemiology and Microbiology of the Ministry of Health of the Russian Federation, Gamaleya st. 18, 123098, Moscow, Russia., Kostyuk SV; Research Centre for Medical Genetics RAMS, Moskvorech'e St. 1, Moscow, 115478, Russia., Schols D; Rega Institute for Medical Research, KU Leuven, Herestraat 49, 3000, Leuven, Belgium., Shestakov AF; IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia and Faculty of Fundamental Physics & Chemical Engineering, Moscow Lomonosov State University, GSP 1, 1-51 Leninskie Gory, Moscow, 119991, Russia., Troshin PA; Skolkovo Institute of Science and Technology, Nobel St. 3, Moscow, 143026, Russia. troshin2003@inbox.ru and IPCP RAS, Semenov Prospect 1, Chernogolovka, 141432, Russia.
Jazyk: angličtina
Zdroj: Organic & biomolecular chemistry [Org Biomol Chem] 2019 Aug 14; Vol. 17 (30), pp. 7155-7160. Date of Electronic Publication: 2019 Jun 06.
DOI: 10.1039/c9ob00593e
Abstrakt: We report an "inversed" Arbuzov reaction of the fullerene derivatives C 60 Ar 5 Cl with trialkyl phosphites P(OR) 3 producing alkylated fullerene derivatives C 60 Ar 5 R (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.
Databáze: MEDLINE