iodine in methanol Kinetics; byproducts: (CH3)3SiC6H4-p-I;

in dichloromethane byproducts: (CH3)3SiC6H4-p-NO; at -25°C;;

n-butyllithium in diethyl ether byproducts: LiCl; n-BuLi added dropwise to 1,4-dibromobenzene soln. at -78°C, allowed to warm to 5°C, Me3SiCl added dropwise at -78°C, stirred for 30 min at room temp., n-C4H9Li added dropwise at -78°C, allowed to warm to 5°C,; Me3SnCl added dropwise at -78°C, allowed to warm, stirred for 1 h at room temp.; washed (H2O), dried (MgSO4), passed through SiO2, solvents removed (vac.); elem. anal.;

magnesium in tetrahydrofuran refluxing for 6 h;;

sodium in diethyl ether; hexane refluxing for 1 h in Ar-atm.; 12 h at 25°C in Ar-atm.;;

in diethyl ether

1: diethyl ether 2: tetrahydrofuran View Scheme

1: diethyl ether 2: tetrahydrofuran View Scheme

tetrakis(triphenylphosphine) palladium(0) in toluene T=125°C; Stille coupling; 48 h;