2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene T=80°C; 2 h;

periodic acid in tetrahydrofuran 3 h;

1: perphthalic acid / diethyl ether / cooling 2: 3.85 g / HIO4 / tetrahydrofuran; diethyl ether / 1.5 h View Scheme

1: 72 percent / triethylamine / acetonitrile / 60 h / Ambient temperature 2: 78 percent / Bu3SnH, AIBN / benzene / 2 h / 80 °C View Scheme

1.1: 92 percent / pyridine / CHCl3 / 0.5 h / sonication 2.1: magnesium / diethyl ether / 0.5 h / 20 °C / sonication 2.2: 95 percent / Li2CuCl4 / diethyl ether; tetrahydrofuran / 0.5 h / -78 - 20 °C / sonication 3.1: perphthalic acid / diethyl ether / cooling 4.1: 3.85 g / HIO4 / tetrahydrofuran; diethyl ether / 1.5 h View Scheme

1.1: magnesium / diethyl ether / 0.5 h / 20 °C / sonication 1.2: 95 percent / Li2CuCl4 / diethyl ether; tetrahydrofuran / 0.5 h / -78 - 20 °C / sonication 2.1: perphthalic acid / diethyl ether / cooling 3.1: 3.85 g / HIO4 / tetrahydrofuran; diethyl ether / 1.5 h View Scheme

1: 1.) Mg / 1.) ether, 2.) ether 2: pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 5 h 3: LiAlH4 / diethyl ether / Ambient temperature 4: MCPBA / CH2Cl2 / 4 h 5: HIO4*2H2O / tetrahydrofuran / 3 h View Scheme

1: pyridine / 1.) 0 deg C, 30 min, 2.) room temp., 5 h 2: LiAlH4 / diethyl ether / Ambient temperature 3: MCPBA / CH2Cl2 / 4 h 4: HIO4*2H2O / tetrahydrofuran / 3 h View Scheme

dibenzoyl peroxide T=80 - 90°C; 10 h;