oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane

cyclohexa-1,4-diene in chlorobenzene T=190°C; 8 h;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 1 h; Heating;

1: 94 percent / LiAlH4 / diethyl ether / 1.) 0 deg C, 5 min, 2.) 20 deg C, 30 min 2: 89 percent / (COCl)2, DMSO, Et3N / CH2Cl2 View Scheme

1: 1.) Mg / 1.) Et2O, 2.) Et2O, r.t., 2 d 2: 1.) 9-BBN, 2.) 30percent aq. H2O2, 6 M aq. NaOH / 1.) THF, r.t., 1 h, 2.) EtOH, r.t., 15 min; 50 deg C, 10 min 3: 68 percent / PCC / CH2Cl2 / 7 h / Ambient temperature 4: 51 percent / n-Bu3SnH, AIBN / benzene / 1 h / Heating View Scheme

1: 67 percent / NBS, benzoyl peroxide / CCl4 / 2 h / Heating 2: 1.) Mg / 1.) Et2O, 2.) Et2O, r.t., 2 d 3: 1.) 9-BBN, 2.) 30percent aq. H2O2, 6 M aq. NaOH / 1.) THF, r.t., 1 h, 2.) EtOH, r.t., 15 min; 50 deg C, 10 min 4: 68 percent / PCC / CH2Cl2 / 7 h / Ambient temperature 5: 51 percent / n-Bu3SnH, AIBN / benzene / 1 h / Heating View Scheme

1: 1.) 9-BBN, 2.) 30percent aq. H2O2, 6 M aq. NaOH / 1.) THF, r.t., 1 h, 2.) EtOH, r.t., 15 min; 50 deg C, 10 min 2: 68 percent / PCC / CH2Cl2 / 7 h / Ambient temperature 3: 51 percent / n-Bu3SnH, AIBN / benzene / 1 h / Heating View Scheme

1: 68 percent / PCC / CH2Cl2 / 7 h / Ambient temperature 2: 51 percent / n-Bu3SnH, AIBN / benzene / 1 h / Heating View Scheme

1: LiAlH4; diethyl ether; THF 2: CrO3; H2SO4; acetone View Scheme