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

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 Full article

Journal

European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690

Output data

Year: 2013, Volume: 2013, Number: 16, Pages: 3347-3355 Pages count : DOI: 10.1002/ejoc.201300176

Tags

Radicals; Carbocations; Quinones; Reaction mechanisms; Synthesis design

Authors

Rogozhnikova Olga Yu ¹ , Vasiliev Vladimir G. ¹ , Troitskaya Tatiana I. ¹ , Trukhin Dmitry V. ¹ , Mikhalina Tatiana V. ¹ , Halpern Howard J. ² , Tormyshev Victor M. ^1,3

Affiliations

1	(Данные Web of science) Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia
2	(Данные Web of science) Univ Chicago, Dept Radiat & Cellular Oncol, Ctr EPR Imaging Vivo Physiol, Chicago, IL 60637 USA
3	(Данные Web of science) Novosibirsk State Univ, Dept Nat Sci, Novosibirsk 630090, Russia

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.

Rogozhnikova O.Y. , Vasiliev V.G. , Troitskaya T.I. , Trukhin D.V. , Mikhalina T.V. , Halpern H.J. , Tormyshev V.M.
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

European Journal of Organic Chemistry. 2013. V.2013. N16. P.3347-3355. DOI: 10.1002/ejoc.201300176 WOS Scopus РИНЦ

Full text from publisher

Published online:	Apr 15, 2013
Published print:	Jun 1, 2013

Web of science	WOS:000320175200016
Scopus	2-s2.0-84878178574
Elibrary	20429981
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