Generation of Trityl Radicals by Nucleophilic Quenching of Tris(2,3,5,6-tetrathiaaryl)methyl Cations and Practical and Convenient Large-Scale Synthesis of Persistent Tris(4-carboxy-2,3,5,6-tetrathiaaryl)methyl Radical.
Tris(2,3,5,6-tetrathiaaryl)methyl cations, which were generated from the corresponding triarylmethanols in the presence of strong acids, underwent reaction with nucleophiles to give trityl radicals, as the product of a one-electron reduction of the carbocation. Depending on the nature of the nucleophile, the only byproducts were either diamagnetic quinone methides or asymmetrical monosubstituted trityl radicals. Herein, we report a protocol for the large-scale synthesis of the Finland trityl, which has the advantage of high overall yield and reproducibility.
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
Olga Yu
OY
Rogozhnikova
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
Vladimir G
VG
Vasiliev
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
Tatiana I
TI
Troitskaya
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
Dmitry V
DV
Trukhin
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
Tatiana V
TV
Mikhalina
The Center for EPR Imaging in vivo Physiology, Department of Radiation and Cellular Oncology, the University of Chicago, Chicago, IL 60637, USA.
Howard J
HJ
Halpern
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia ; Department of Natural Sciences, Novosibirsk State University, 2 Pirogov St., Novosibirsk 630090, Russia.
Victor M
VM
Tormyshev
Carbocations; Quinones; Radicals; Reaction mechanisms; Synthesis design