860709-64-4Relevant academic research and scientific papers
Terphenyl crowns: A new family of receptors containing ethereal canopies that direct potassium cation onto benzenoid platforms for cation-π interactions
Shukla, Ruchi,Lindeman, Sergey V.,Rathore, Rajendra
, p. 5600 - 5602 (2009)
We have synthesized three simple and versatile terphenyl crowns (TC) receptors containing ethereal canopies that direct a potassium cation for efficient cation-π interactions as established by 1H NMR spectroscopy and by isolation and X-ray crystallography of their K+ salts.
Controlling the Scholl reaction
King, Benjamin T.,Kroulik, Jiri,Robertson, Charles R.,Rempala, Pawel,Hilton, Cameron L.,Korinek, Justin D.,Gortari, Lisa M.
, p. 2279 - 2288 (2008/02/01)
Guidelines for the application of the Scholl reaction were developed. Labeling experiments demonstrate that the Scholl reaction fails in small, unsubstituted oligophenylenes (e.g., o-terphenyl) due to oligomerization of the products (e.g., triphenylene). Incorporation of suitably placed blocking groups (e.g., t-butyl) suppresses oligomerization. The well-established directing group effects in electrophilic aromatic substitution predict the outcome of Scholl reactions of substituted substrates. Activating o,p-directing groups (e.g., MeO) direct bond formation o,p, either intramolecularly or intermolecularly. Deactivating o,p-directing groups (e.g., Br) also direct bond formation o,p but yields are lower. Deactivating m-directors (e.g., NO2) suppress reaction. MoCl5 and PhI(OOCCF3)2/BF 3·Et2O are general and effective reagents for the Scholl oxidation. Calculations (B3LYP/6-31G(d)) predict the Scholl reaction in alkoxyarenes to proceed via arenium cations, not radical cations. Suzuki-Miyaura couplings were used to generate 12 substituted o-terphenyl derivatives.
