FACILE AROMATIC NUCLEOPHILIC SUBSTITUTIONS OBSERVED FOR THE TRIARYLCARBENIUM IONS, [(4-YC6H4)PHI-C-2](+) [PHI=2,6-(MEO)(2)C6H3 Y=MEO, CL, ME(2)N, HO]

Triarylmethanols of type (4-YC6H4)Phi(2)COH {Phi=2,6-(MeO)(2)C6H3; Y=MeO, Cl, Me(2)N} were prepared. The methanol, (4-MeOC(6)H(4))Phi(2)COH, reacted with acids in a variety of solvents to give the triaryl-carbenium salts, [(4-MeOC(6)H(4))Phi(2)C]X or [(4-HOC6H4)Phi(2)C]X, or 4-bis(2,6-dimethoxyphenyl)methylene-2,5-cyclohexadienone, O=C6H4=C Phi(2), depending on the conditions. These carbenium salts further reacted in alcohols, ROH, to give the triarylmethanes, (4-ROC(6)H(4))Phi(2)CH (R=Me, Et), where the para-substituent, MeO or HO, was substituted by the solvent, accompanied by a reduction at the central carbon. The methanol, (4-ClC6H4)Phi(2)COH, also reacted with acid to give the carbenium salt or the triarylmethane, depending on the conditions. While the methanol, (4-Me(2)NC(6)H(4))Phi(2)COH, also gave the carbenium salt, [(4-Me(2)NC(6)H(4))Phi(2)C]X, it was inert against the formation of the triarylmethane under analogous conditions. It reacted with aqueous sodium hydroxide to give O=C6H4=C Phi(2) rather than the original methanol. The para-substituent of [(4-MeOC(6)H(4))Phi(2)C]X was substituted by di- and monoalkylamines, RR'NH, to give [(4-RR'NC6H4) Phi(2)C]X (R,R'=Me,Me; Et,Et; Me,H; Et,H; Bu,H). While [(4-ClC6H4)Phi(2)C]X reacted with the dialkylamines to give [(4-RR'NC6H4)Phi(2)C]X, it reacted with monoalkylamines, RNH(2), to give [(4-ClC6H4)Phi(2)C-NRH(2)]X. [(4-Me(2)NC(6)H(4)) Phi(2)C]X was hydrolyzed in the presence of diethylamine to give O=C6H4=C Phi(2), but reacted with monoalkylamines to give RN=C6H4=C Phi(2).