1: 1.) n-butyllithium / 1.) THF, 1 h, 2.) 25 min 2: 36 percent / PBr3 / benzene / 2.5 h / 75 °C 3: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 4: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme

1: 58 percent / Br2, AlCl3 / CH2Cl2 / 18 h / Ambient temperature 2: 56 percent / AlCl3 / benzene / 1 h / Ambient temperature 3: 1.) n-butyllithium / 1.) THF, 1 h, 2.) 25 min 4: 36 percent / PBr3 / benzene / 2.5 h / 75 °C 5: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 6: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme

1: 56 percent / AlCl3 / benzene / 1 h / Ambient temperature 2: 1.) n-butyllithium / 1.) THF, 1 h, 2.) 25 min 3: 36 percent / PBr3 / benzene / 2.5 h / 75 °C 4: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 5: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme

1: 36 percent / PBr3 / benzene / 2.5 h / 75 °C 2: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 3: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme

methanesulfonic acid; palladium on activated charcoal 1.) CHCl3, r.t., 2.) triglyme, reflux; Yield given. Multistep reaction;

1: 1.) ethylmagnesium bromide / 1.) THF, ether, reflux, 3 h, 2.) reflux 2: 1.) methanesulfonic acid / 2.) 10 percent Pd/C / 1.) CHCl3, r.t., 2.) triglyme, reflux View Scheme

9H-fluoren-9-one in chloroform 72 h; Inert atmospherePhotolysis;

copper-turnings; iron T=650°C;

1: dimethylformamide 2: NaOEt / ethanol 3: dehydrobenzene; CH2Cl2 View Scheme

1: NaOEt / ethanol 2: dehydrobenzene; CH2Cl2 View Scheme