Synthesis and Isolation of Polytrityl Cations by Utilizing Hexaphenylbenzene and Tetraphenylmethane Scaffolds

• Published in: Journal of organic chemistry Vol. 69; no. 5; pp. 1524 - 1530
• Main Authors: Rathore, Rajendra, Burns, Carrie L, Guzei, Ilia A
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.03.2004; Amer Chemical Soc
• Subjects: Aliphatic, non-condensed and condensed benzenic, and alicyclic compounds; Chemistry; Chemistry, Organic; Condensed matter: structure, mechanical and thermal properties; Exact sciences and technology; Noncondensed benzenic compounds; Organic chemistry; Organic compounds; Physical Sciences; Physics; Preparations and properties; Science & Technology; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; POLYMERIZATION; ELECTRON-TRANSFER; CARBOCATIONS; STABILITY; BEHAVIOR; Organic cation; Crystal form; Stability; Molecular structure; NMR spectrometry; Hydride transfer; Hydrogen 1; Soluble compound; Aromatic compound; Chemical reactivity; Chemical synthesis; Carbon 13; Ultraviolet visible spectrometry; Organic synthesis; Polycation; Benzenic compound; X ray diffraction; Crystalline structure
• ISSN: 0022-3263; 1520-6904
• DOI: 10.1021/jo035598i

The successful isolation of stable (and soluble) hexa- and tetratrityl cations based on hexaphenylbenzene and tetraphenylmethane scaffold has been accomplished by using readily available starting materials. These robust polytrityl cations can be isolated in crystalline form and stored indefinitely at 0 °C. Their structures have been established by 1H/13C NMR spectroscopy and by UV−vis spectroscopy. The structures of these polytrityl cations were further confirmed by quantitative transformations to the reduced (poly)triphenylmethyl derivatives by hydride transfer from triethylsilane, cycloheptatriene, or a borane−dimethyl sulfide complex.