Preparation of Diversely Substituted Triarylmethyl Radicals by the Quenching of Tris(2,3,5,6-tetrathiaaryl)methyl Cations with C-, N-, P-, and S-Nucleophiles

Victor M Tormyshev; Olga Yu Rogozhnikova; Michael K Bowman; Dmitry V Trukhin; Tatiana I Troitskaya; Vladimir G Vasiliev; Leonid A Shundrin; Howard J Halpern

doi:10.1002/ejoc.201301161

Preparation of Diversely Substituted Triarylmethyl Radicals by the Quenching of Tris(2,3,5,6-tetrathiaaryl)methyl Cations with C-, N-, P-, and S-Nucleophiles

European J Org Chem. 2014 Jan 1;2014(2):371-380. doi: 10.1002/ejoc.201301161.

Authors

Victor M Tormyshev¹, Olga Yu Rogozhnikova², Michael K Bowman³, Dmitry V Trukhin², Tatiana I Troitskaya², Vladimir G Vasiliev², Leonid A Shundrin², Howard J Halpern⁴

Affiliations

¹ Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia, http://www.nioch.nsc.ru/eng/labs/mcg_e.htm ; Department of Natural Sciences, National Research University, Novosibirsk State University, 2 Pirogov St., Novosibirsk 630090, Russia.
² Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia, http://www.nioch.nsc.ru/eng/labs/mcg_e.htm.
³ Department of Chemistry, The University of Alabama, Box 870336, Tuscaloosa, Alabama 35487-0336, USA.
⁴ The Center for EPR Imaging in vivo Physiology, Department of Radiation and Cellular Oncology, The University of Chicago, Chicago, IL 60637, USA, http://epri.uchicago.edu/

Abstract

C-, N-, P-, and S-nucleophiles reacted with symmetrical tris(2,3,5,6-tetrathiaaryl)methyl cations, generated from the corresponding triarylmethanols by strong acids, to give a variety of asymmetrical monosubstituted persistent triaryl-methyl (TAM) radicals as the major products. The only byproducts were symmetrical TAMs.

Keywords: Carbocations; Electron transfer; Nucleophilic addition; Radicals; Reaction mechanisms.

Abstract

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