tris-(2-cyanoethyl)-phosphine in toluene 4 h; Heating;

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 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 View Scheme

1: 85 percent / KOH / methanol; CH2Cl2 / Ambient temperature 2: 90 percent / P(CH2CH2CN)3 / toluene / 4 h / Heating 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 View Scheme

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