1: With n-butyllithium; N,N,N',N,-tetramethylethylenediamine in tetrahydrofuran; hexane T=-78°C; 1.5 h; Inert atmosphere; 2: With iodine in tetrahydrofuran; hexane T=-78 - 20°C; 0.5 h;

1.1: tert-butyl alcohol / 30 °C 2.1: n-butyllithium; N,N,N',N,-tetramethylethylenediamine / hexane; tetrahydrofuran / 1.5 h / -70 °C / |Inert atmosphere 2.2: 0.5 h / -78 °C / |Inert atmosphere View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -5 °C / Inert atmosphere 1.2: 1 h 2.1: N,N,N',N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran; hexanes / 1.33 h / -78 °C 2.2: 1.5 h / -78 - 20 °C View Scheme

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -5 °C / Inert atmosphere 1.2: 1 h 2.1: N,N,N',N,-tetramethylethylenediamine; n-butyllithium / tetrahydrofuran; hexanes / 1.33 h / -78 °C 2.2: 1.5 h / -78 - 20 °C View Scheme

hydrogen bromide T=100°C; 0.166667 h;