n-butyllithium; tri-isopropoxy-borane

hydrogenchloride in tetrahydrofuran

hydrogenchloride; n-butyllithium in diethyl ether; hexane BuLi soln. (hexane) addn. to org. compd. soln. (Et2O) at 0°C, mixt. addn. to B-compd. soln. (Et2O) at -78°C over 30 min, stirring 3 h at -50 to -70°C and 60 h at room temp., 2 M HCl addn., stirring 2 h, org. phase sepn.; org. phase washing (water), drying (MgSO4), treating with charcoal, ethereal soln. concn. to dryness, residue vac. drying at 50°C;

1: 1-Bromopyrene With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 0.5 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78 - 20°C; 0.5 h; 3: 2,3-dimethylbutane-2,3-diol in diethyl ether; hexane T=40°C; 0.75 h;

n-butyllithium in diethyl ether 1) 1.1 rquiv. of butyllithium at 0°C for 30.min, 2) 5 equiv. of Bcompd. 6 h at -78°C, for 20 h at room temp., 3) H3O(1+), at room temp. for 3 h;

hydrogenchloride in water T=20°C;

1: N-bromosuccinmide; dibenzoyl peroxide / N,N-dimethyl-formamide / 20 °C 2: n-butyllithium / tetrahydrofuran / -78 °C 3: hydrogenchloride / water / 20 °C View Scheme

in diethyl ether; dichloromethane T=20°C; 24 h;

tetrakis(triphenylphosphine) palladium(0); potassium hydroxide in tetrahydrofuran; water 48 h; RefluxInert atmosphere;

caesium carbonate in 1-methyl-pyrrolidin-2-one; water T=100°C; 10 h;