p-benozquinone; (SIPr)Pd(OAc)2(H2O) in methanol T=20°C; 24 h;

1: 1-n-butyl-3-iodobicyclolt;1.1.1gt;pentane With tert.-butyl lithium; zinc(II) chloride in tetrahydrofuran T=25°C; Metallation; 1 h; 2: 4-(trimethylsilyl)bromobenzene With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride in tetrahydrofuran T=25°C; Substitution; 24 h; Further stages.;

sodium

1: (i) nBuLi, Et2O, benzene, (ii) /BRN= 1209232/ 2: Na / toluene View Scheme

sodium in toluene

in dichloromethane Irradiation (UV/VIS); mixing equimolar amts. of educts in CH2Cl2; irradiation , 16°C, 5h (313 nm); chromy. (silica gel, CH2Cl2); identification by MS;

in dichloromethane Irradiation (UV/VIS); mixing equimolar amts. of educts in CH2Cl2; irradiation , 16°C, 5h (313 nm); chromy. (silica gel, CH2Cl2); identification by MS;

lead(IV) acetate; boron trifluoride diethyl etherate in chloroform 1.) 10 deg C, 2 h; 2.) RT, 24 h;