tributylphosphine in chloroform-d1 T=100°C; 1 h;

1: (i) tBuLi, Me2NCH2CH2NMe2, THF, (ii) /BRN= 956591/ 2: nBu3P / CDCl3 / 1 h / 100 °C View Scheme

1: pyridinium tribromide / CH2Cl2 / 0.5 h / Ambient temperature 2: P4S10 / toluene / 0.17 h / Heating 3: 85 percent / KOH / methanol; CH2Cl2 / Ambient temperature 4: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 5: 1) n-BuLi / multistep reaction; also with CO2, HC(O)NMe2, PhCO2Et, ClSiMe3 View Scheme

1: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 2: 1) n-BuLi / multistep reaction; also with CO2, HC(O)NMe2, PhCO2Et, ClSiMe3 View Scheme

1: P4S10 / toluene / 0.17 h / Heating 2: 85 percent / KOH / methanol; CH2Cl2 / Ambient temperature 3: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 4: 1) n-BuLi / multistep reaction; also with CO2, HC(O)NMe2, PhCO2Et, ClSiMe3 View Scheme

1: 85 percent / KOH / methanol; CH2Cl2 / Ambient temperature 2: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 3: 1) n-BuLi / multistep reaction; also with CO2, HC(O)NMe2, PhCO2Et, ClSiMe3 View Scheme

1: m-chloroperbenzoic acid / CH2Cl2 / 0 °C 2: pyridinium tribromide / CH2Cl2 / 0.5 h / Ambient temperature 3: P4S10 / toluene / 0.17 h / Heating 4: 85 percent / KOH / methanol; CH2Cl2 / Ambient temperature 5: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 6: 1) n-BuLi / multistep reaction; also with CO2, HC(O)NMe2, PhCO2Et, ClSiMe3 View Scheme

n-butyllithium 1) THF, -100 deg C, 30 min, 2) THF, -100 deg C, 30 min; Yield given. Multistep reaction;