52856-25-4Relevant academic research and scientific papers
Facile Aromatic Nucleophilic Substitutioins Observed for the Triarylcarbenium Ions, +
Wada, Masanori,Watanabe, Tetsuya,Natsume, Satoko,Mishima, Hisashi,Kirishima, Katsuhiko,Erabi, Tatsuo
, p. 3233 - 3240 (2007/10/03)
Triarylmethanols of type (4-YC6H4)Φ2COH were prepared.The methanol, (4-MeOC6H4)Φ2COH, reacted with acids in a variety of solvents to give the triarylcarbenium salts, X or X, or 4-bis(2,6-dimethoxyphenyl)methylene-2,5-cyclohexadienone, O=C6H4=CΦ2, depending on the conditions.These carbenium salts further reacted in alcohols, ROH, to give the triarylmethanes, (4-ROC6H4)Φ2CH (R=Me, Et), where the para-substituent, MeO or HO, was substituted by the solvent, accompanied by a reduction at the central c arbon.The methanol, (4-ClC6H4)Φ2COH, also reacted with acid to give the carbenium salt or the triarylmethane, depending on the conditions.While the methanol, (4-Me2NC6H4)Φ2COH, also gave the carbenium salt, -X, it was inert against the formation of the triarylmethane under analogous conditions.It reacted with aqueous sodium hydroxide to give O=C6H4=CΦ2 rather than the original methanol.The para-substituent of X was substituted by di- and monoalkylamines, RR'NH, to give X (R,R'=Me,Me; Et,Et; Me,H; Et,H; Bu,H).While X reacted with the dialkylamines to give X, it reacted with monoalkylamines, RNH2, to give X. X was hydrolyzed in the presence of diethylamine to give O=C6H4=CΦ2, but reacted with monoalkylamines to give RN=C6H4=CΦ2.
