REGIOSPECIFIC SYNTHESIS OF AROMATIC COMPOUNDS VIA ORGANOMETALLIC INTERMEDIATES. I. para-SUBSTITUTED BENZENES

Article abstract of DOI:10.1016/S0022-328X(00)99496-8

Para-substituted benzene compounds, p-XC6H4X' (X = CF3C(O) and X' = CH3, CO2H, C(O)CF3, C(O)CH3, C(O)H and SH) have been prepared via sequential metal-halogen exchange reactions between p-BrC6H4Br and n-C4H9Li and the appropriate electrophiles.Low reaction temperature is critical to stabilization of the various intermediates.The CF3 group has a pronounced effect on providing stability to the lithium hemiketal intermediates.