1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr 3: 81 percent / PdCl2dppf / diethyl ether / Heating 4: 0.36 g / NBS; AgNO3 / acetone / 10 h / 25 °C 5: 0.27 g / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 15514.9 Torr 6: PdCl2dppf / diethyl ether / Heating 7: NaH; MeOH / tetrahydrofuran / 2 h 8: 64 percent / 1,4-cyclohexadiene / benzene / 160 °C / 12411.9 Torr View Scheme

potassium carbonate in tetrahydrofuran; methanol T=25°C; 0.5 h; Inert atmosphere;

1: 100 percent / NBS; AgNO3 / acetone / 10 h / 25 °C 2: 70 percent / 1,4-cyclohexadiene; N2 / benzene / 2 h / 180 °C / 18100.7 Torr View Scheme

1: 85 percent / KF / H2O; dimethylformamide / 4 h / 25 °C 2: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) -78 to 25 deg C, 47.5 h 3: 31 percent / CBr4 / 36 h / Heating View Scheme

1: 98 percent / potassium fluoride / H2O; dimethylformamide / 4 h / Ambient temperature 2: 1.) ethylmagnesium bromide / 1.) ethylmagnesium bromide, THF, 1.5 h. 20 deg C 2.) 1.5 h, room temp View Scheme

1: 85 percent / KF / H2O; dimethylformamide / 4 h / 25 °C 2: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) -78 to 25 deg C, 47.5 h 3: 1,4-cyclohexadiene / benzene-d6 / 84 °C / τ1/2, other trapping agents; other o-dialkynylarenes View Scheme

1: 86 percent / potassium carbonate / methanol 2: 86 percent / n-BuNH2; CuI / Pd(PPh3)4 / diethyl ether / 6 h View Scheme

in hexane (Ar); soln. of Ga compd. and alkyne in hexane was treated with amine at room temp.; stirred under reflux for 16 h; cooled to room temp.; decanted; washed (hexane); crystd. (cyclopentane);elem. anal.;

1: 85 percent / KF / H2O; dimethylformamide / 4 h / 25 °C 2: 1) n-BuLi / 1) THF, -78 deg C, 1 h, 2) -78 to 25 deg C, 47.5 h 3: 57 percent / CBr4, C6D6 / 4 h / 150 °C View Scheme