carbon tetrabromide; triphenylphosphine in tetrachloromethane T=20°C; 3 h;

1: 84 percent / LiAlH4 / diethyl ether / 3 h / -78 °C 2: 85 percent / Ph3P; CBr4 / CCl4 / 3 h / 20 °C View Scheme

1.1: 86 percent / 3 h / 160 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 6.1: pyridine / CH2Cl2 / 1 h / 0 °C 7.1: CH2Cl2 / 5 h / 20 °C 8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C 13.1: 30 percent / m-CPBA / CHCl3 / 5 h / -10 - 0 °C View Scheme

1.1: 86 percent / 3 h / 160 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: 86 percent / tetrahydrofuran; hexane / 12 h / -78 - 20 °C 3.1: (1R)-(+)-pinene; BH3*DMS / tetrahydrofuran / 0.5 h / 20 °C 3.2: 78 percent / lithium hydroxide; sodium perborate / tetrahydrofuran; H2O / 2 h / 20 °C 4.1: 94 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / -78 - 0 °C 5.1: diisopropylamine; n-butyllithium / tetrahydrofuran; hexane / 1.25 h / -78 - -40 °C 5.2: 59 percent / ZnCl2 / tetrahydrofuran; hexane; diethyl ether / 0.25 h / -78 °C 6.1: pyridine / CH2Cl2 / 1 h / 0 °C 7.1: CH2Cl2 / 5 h / 20 °C 8.1: 0.67 g / acetic acid / tetrahydrofuran; H2O / 3 h / 0 °C 9.1: 72 percent / magnesium bromide; nitromethane; 1-butanethiol / diethyl ether / 1 h / 20 °C 10.1: 2,4,6-trichlorobenzoyl chloride; triethylamine / tetrahydrofuran / 1 h / 0 °C 10.2: 0.14 g / DMAP / toluene; tetrahydrofuran / 4 h / 20 °C 11.1: 92 percent / zinc; ammonium chloride / methanol / 0.33 h / Heating 12.1: 95 percent / hydrogen fluoride-pyridine / tetrahydrofuran / 16 h / 20 °C View Scheme

T=160°C; 3 h;