通过亲核淬灭三（2,3,5,6 - 四硫芳基）甲基阳离子生成三苯甲基自由基以及持久的三（4 - 羧基 - 2,3,5,6 - 四硫芳基）甲基自由基的实用便捷大规模合成
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.
作者信息
Rogozhnikova Olga Yu, Vasiliev Vladimir G, Troitskaya Tatiana I, Trukhin Dmitry V, Mikhalina Tatiana V, Halpern Howard J, Tormyshev Victor M
机构信息
Vorozhtsov Novosibirsk Institute of Organic Chemistry, 9 Acad. M.A. Lavrentjev Ave., Novosibirsk 630090, Russia.
The Center for EPR Imaging in vivo Physiology, Department of Radiation and Cellular Oncology, the University of Chicago, Chicago, IL 60637, USA.
出版信息
European J Org Chem. 2013 Jun 1;2013(16):3347-3355. doi: 10.1002/ejoc.201300176.
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.
摘要
三（2,3,5,6 - 四硫芳基）甲基阳离子是在强酸存在下由相应的三芳基甲醇生成的，它与亲核试剂反应生成三苯甲基自由基，这是碳正离子单电子还原的产物。根据亲核试剂的性质，唯一的副产物要么是抗磁性的醌甲基化物，要么是不对称单取代的三苯甲基自由基。在此，我们报道了一种大规模合成芬兰三苯甲基的方法，该方法具有总产率高和可重复性的优点。
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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.通过亲核淬灭三（2,3,5,6 - 四硫芳基）甲基阳离子生成三苯甲基自由基以及持久的三（4 - 羧基 - 2,3,5,6 - 四硫芳基）甲基自由基的实用便捷大规模合成
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