1: 1.) LDA, HMPA / 1.) THF, -78 deg C 2: Al(Hg) / tetrahydrofuran; H2O 3: 94 percent / pyridine / tetrahydrofuran / Heating 4: 1.) n-BuLi, TMEDA, 2.) DMF 5: 1.) Et2O, pentane, -78 deg C, 2.) DMAP, 20 deg C 6: 56 percent / LICA / tetrahydrofuran / -78 deg C to 20 deg C 7: 94 percent / K2CO3 / acetone 8: 1.) LICA / 1.) THF, 0 deg C, 2.) 0 deg C 9: 1.) KOH, 2.) aq. oxalic acid, silicagel / 1.) MeOH, 2.) CH2Cl2, 20 deg C 10: 1.) O3, 2.) CF3COOH / 1.) MeOH, -78 deg C, 2.) CHCl3, H2O View Scheme

3-chloro-benzenecarboperoxoic acid in dichloromethane T=-78°C;

1: 84 percent / tetrahydrofuran / 18 h / Heating 2: 90 percent / mCPBA / CH2Cl2 / 2 h / -30 °C View Scheme

1: 94 percent / 30percent H2O2; LiOH / methanol / 8 h / 25 °C 2: 84 percent / tetrahydrofuran / 18 h / Heating 3: 90 percent / mCPBA / CH2Cl2 / 2 h / -30 °C View Scheme

3-chloro-benzenecarboperoxoic acid; lithium diisopropyl amide 1.) THF, - 78 deg C; 2.) CH2Cl2, -78 deg C; Yield given. Multistep reaction;

1: 0.75 g / NH4Cl / H2O / 1 h / Ambient temperature 2: 0.80 g / 85percent m-chloroperbenzoic acid / CH2Cl2 / 3 h / -78 °C View Scheme

1: 1)NaH / 1)THF, room temp., 0.5 h 2)reflux, 24 h 2: 0.75 g / NH4Cl / H2O / 1 h / Ambient temperature 3: 0.80 g / 85percent m-chloroperbenzoic acid / CH2Cl2 / 3 h / -78 °C View Scheme

1: LDA / -78 °C 2: mCPBA / CH2Cl2 / -78 °C View Scheme

1: LDA / -78 °C 2: mCPBA / CH2Cl2 / -78 °C View Scheme

lithium diisopropyl amide 1) THF, HMPA, -40 to -35 deg C, 2 h, 2) THF, HMPA, -40 to -35 deg C, 2 h; Yield given. Multistep reaction;