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

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.