piperidinium acetate in benzene Heating;

1: diethyl ether / Ambient temperature 2: 62.6 percent / n-BuLi, tetramethylethylenediamine / hexane / 1.) -55 deg C to room temperature, 2.) 0 deg C, 1 h View Scheme

1: KH / dimethylsulfoxide / 0.5 h 2: diethyl ether / Ambient temperature 3: 62.6 percent / n-BuLi, tetramethylethylenediamine / hexane / 1.) -55 deg C to room temperature, 2.) 0 deg C, 1 h View Scheme

1: 23.3 g / H2O / acetic acid; trifluoroacetic acid / 2.5 h / 75 °C 2: 65 percent / KCH2SOCH3 / dimethylsulfoxide / 1.) 12 deg C, 1 h, 2.) 12 deg C -< RT, 1 h 3: toluene / 5 h / 0 °C 4: 1.26 g / K2CO3 / CH2Cl2 / 2 h / -78 °C 5: 1) m-chloroperbenzoic acid, 2.) diisopropylamine / 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT View Scheme

1: 98 percent / 1.) lithium diisopropylamide / tetrahydrofuran / 0.25 h / -78 °C 2: 58 percent / n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 3: toluene / 5 h / 0 °C 4: 1.26 g / K2CO3 / CH2Cl2 / 2 h / -78 °C 5: 1) m-chloroperbenzoic acid, 2.) diisopropylamine / 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT View Scheme

1: 58 percent / n-BuLi / diethyl ether; hexane / 0.5 h / -78 °C 2: toluene / 5 h / 0 °C 3: 1.26 g / K2CO3 / CH2Cl2 / 2 h / -78 °C 4: 1) m-chloroperbenzoic acid, 2.) diisopropylamine / 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT View Scheme

1: 1.26 g / K2CO3 / CH2Cl2 / 2 h / -78 °C 2: 1) m-chloroperbenzoic acid, 2.) diisopropylamine / 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT View Scheme

n-butyllithium; N,N,N',N,-tetramethylethylenediamine in hexane 1.) -55 deg C to room temperature, 2.) 0 deg C, 1 h;

diisopropylamine; 3-chloro-benzenecarboperoxoic acid 1.) -78 deg C, 30 min, 2.) -78 deg C -> RT; Yield given. Multistep reaction;

1: 84 percent / DIBAH / diethyl ether; benzene / 1.5 h / 0 °C 2: 70 percent / pyrrolidine; glac. HOAc / benzene / 1.5 h / Heating View Scheme