2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 7 h; Heating;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 15 h; Heating;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride; phosphorous acid trimethyl ester Further byproducts. Title compound not separated from byproducts.;

1: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h 2: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 3: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 4: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

1: NaBH4 / methanol / Ambient temperature 2: toluene-p-sulfonic acid / toluene / 4 h / Heating 3: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h 4: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 5: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 6: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

1: 51.4 percent / NaBH4 / ethanol / 6 h 3: NaBH4 / methanol / Ambient temperature 4: toluene-p-sulfonic acid / toluene / 4 h / Heating 5: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h 6: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 7: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 8: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

2: NaBH4 / methanol / Ambient temperature 3: toluene-p-sulfonic acid / toluene / 4 h / Heating 4: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h 5: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 6: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 7: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

1: 1) NaH / 1) toluene, reflux, 30 min, 2) reflux, 1 h 2: 51.4 percent / NaBH4 / ethanol / 6 h 4: NaBH4 / methanol / Ambient temperature 5: toluene-p-sulfonic acid / toluene / 4 h / Heating 6: 96 percent / diisobutylaluminium hydride / diethyl ether; hexane / 1) -78 deg C to room temperature, 2) room temperature, 8 h 7: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 8: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 9: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

1: 91.3 percent / N-bromosuccinimide, Me2S / CH2Cl2 / 1) -30 deg C, 3 h, 2) room temperature, 1 h 2: 44.7 percent / m-chloroperbenzoic acid / CH2Cl2 / 1) 0 deg C, 1 h, 2) room temperature, 12 h 3: 33 percent / Bu3SnH, azoisobutyronitrile / benzene / 15 h / Heating View Scheme

T=333°C;