1: 64 percent / Fe acetylacetonate / bis-(2-methoxy-ethyl) ether; diethyl ether; liquid ammonia / from -30 to 30 deg C, 5 h, 30 deg C, 15 h 2: 82 percent / Br2, triphenylphosphine, (C2H5)3N / CCl4 / 12 h / 20 °C 3: 74 percent / CuI, bi-2-pyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) room temperature, 12 h 4: 1) 9-borabicyclo<3.3.1>nonane, 2) CH3CO2H / 1) THF, 0 deg C, 24 h, 2) reflux, 5 h View Scheme

boron trifluoride diethyl etherate in tetrahydrofuran T=-78°C; 0.5 h;

sodium hydroxide; dihydrogen peroxide; iodine in tetrahydrofuran; diethyl ether 1.) -78 deg C, 3 h, 2.) 55 deg C, 1 h; MechanismProduct distribution;

iron (III) acetylacetonate in diethyl ether; diethylene glycol dimethyl ether; ammonia from -30 to 30 deg C, 5 h, 30 deg C, 15 h;

1: 64 percent / Fe acetylacetonate / bis-(2-methoxy-ethyl) ether; diethyl ether; liquid ammonia / from -30 to 30 deg C, 5 h, 30 deg C, 15 h 2: 82 percent / Br2, triphenylphosphine, (C2H5)3N / CCl4 / 12 h / 20 °C 3: 74 percent / CuI, bi-2-pyridyl / tetrahydrofuran / 1) 2 deg C, 2 h, 2) room temperature, 12 h View Scheme