期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2013, 期 16, 页码 3347-3355出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201300176
关键词
Radicals; Carbocations; Quinones; Reaction mechanisms; Synthesis design
资金
- Russian Foundation for Basic Research [13-04-00680A]
- Ministry of Education and Science of the Russian Federation [8466]
- National Institute of Biomedical Imaging and Bioengineering, National Institute of Health (NIH) [5P41EB002034]
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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