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

Overview

Journal European J Org Chem

Specialty Biochemistry

Date 2014 Apr 29

PMID 24772001

Citations 17

Authors

Olga Yu Rogozhnikova

Vladimir G Vasiliev

Tatiana I Troitskaya

Dmitry V Trukhin

Tatiana V Mikhalina

Howard J Halpern

Victor M Tormyshev

Affiliations

Soon will be listed here.

Abstract

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.

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