sodium tetrahydroborate in methanol; water

1: With tris[3,5-bis(2,2'',6,6''-tetramethyl-m-terphenyl-5'-yl)phenyl]phosphine; copper(l) chloride; sodium t-butanolate in toluene T=20°C; 2 h; Inert atmosphere; 2: With hydrogenchloride; methanol in toluene Inert atmosphere;

Sodium bromate; sodium hydrogensulfite in water; acetonitrile T=21°C; pH=1.7; 2 h;

1: cyclohexanol, 2,2,6,6-tetramethyl With potassium hydride in tetrahydrofuran T=25°C; 1 h; 2: allyl bromide in tetrahydrofuran; dimethyl sulfoxide T=0°C; 1 h;

1.1: KH / tetrahydrofuran / 1 h / 25 °C 1.2: 92 percent / tetrahydrofuran; dimethylsulfoxide / 1 h / 0 °C 2.1: 78 percent / 3-chloroperbenzoic acid / CH2Cl2 / 0 - 25 °C View Scheme

1.1: KH / tetrahydrofuran / 1 h / 25 °C 1.2: 92 percent / tetrahydrofuran; dimethylsulfoxide / 1 h / 0 °C 2.1: 78 percent / 3-chloroperbenzoic acid / CH2Cl2 / 0 - 25 °C 3.1: 86 percent / CuI / tetrahydrofuran / 0 - 25 °C 4.1: 88 percent / pyridinium chlorochromate / CH2Cl2 / 0.5 h / 25 °C View Scheme

1.1: KH / tetrahydrofuran / 1 h / 25 °C 1.2: 92 percent / tetrahydrofuran; dimethylsulfoxide / 1 h / 0 °C 2.1: 78 percent / 3-chloroperbenzoic acid / CH2Cl2 / 0 - 25 °C 3.1: 86 percent / CuI / tetrahydrofuran / 0 - 25 °C View Scheme