n-butyllithium in diethyl ether; hexane T=-75°C; 0.25 h;

1: 91 percent / sec-butyllithium / tetrahydrofuran; cyclohexane / 1.5 h / -75 °C 2: 95 percent / bromine / CCl4 / Heating 3: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 4: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 5: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 2: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 3: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: 92 percent / diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 2: 93 percent / bromine / CCl4 / 36 h / Heating 3: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 4: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 5: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: 93 percent / bromine / CCl4 / 36 h / Heating 2: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 3: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 4: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: 95 percent / bromine / CCl4 / Heating 2: diisopropylamine; butyllithium / hexane; tetrahydrofuran / 2 h / -75 °C 3: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 4: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 2: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

1: 92 percent / butylmagnesium chloride; butyllithium / tetrahydrofuran; hexane; toluene / 0.75 h / 0 °C 2: 89 percent / butyllithium / diethyl ether; hexane / 0.25 h / -100 °C 3: 93 percent / butyllithium / diethyl ether; hexane / 0.25 h / -75 °C View Scheme

2: Mg View Scheme

1,10-phenanthroline; nickel dichloride; zinc in water; N,N-dimethyl-formamide T=50°C; Hydrodefluorination; 6 h; Product distribution; Further Variations:ReagentsTemperaturesreaction time;