1.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 18 h / 20 °C 2.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl3; AIBN / 0.08 h / Heating 3.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C 4.1: 92 percent / imidazole / dimethylformamide / 20 °C 5.1: t-BuLi / pentane / 0.5 h / -78 °C 5.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C 6.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C 7.1: 67 percent / 450 °C / 0 Torr 8.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure 9.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C 10.1: 85 percent / n-Bu4NF / tetrahydrofuran / 2 h / 0 °C View Scheme

1.1: oxalyl chloride / dimethylformamide; CH2Cl2 / 18 h / 20 °C 2.1: 1.6 g / 2-mercaptopyridine oxide sodium salt; BrCCl3; AIBN / 0.08 h / Heating 3.1: 77 percent / copper bronze / dimethylformamide / 20 h / 100 °C 4.1: 92 percent / imidazole / dimethylformamide / 20 °C 5.1: t-BuLi / pentane / 0.5 h / -78 °C 5.2: 53 percent / pentane; tetrahydrofuran / 0.5 h / -78 °C 6.1: 75 percent / NaBH3CN; Cl2CHCO2H / various solvent(s) / 0.5 h / -25 °C 7.1: 67 percent / 450 °C / 0 Torr 8.1: 75 percent / H2 / Pt/C / ethyl acetate / atmospheric pressure 9.1: 80 percent / m-chloroperbenzoic acid / CH2Cl2 / 1 h / 20 °C View Scheme