(SPY-5-31)-dichloro-(κ2(C,O)-(2-isopropyloxybenzylidene))(1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidene)ruthenium in toluene T=50°C; 8 h; Glove box;

potassium tert-butylate in tetrahydrofuran; dimethyl sulfoxide T=20°C; 0.166667 h;

1.1: LAH 2.1: H2 / Pd(OH)2 3.1: Et3N / methanol / 2 h / Heating 4.1: pyridine / CH2Cl2 / 20 °C 5.1: LiBr / acetone / Heating 6.1: sodium sulfide nonahydrate / ethanol / Heating 7.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 7.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 8.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1.1: H2 / Pd(OH)2 2.1: Et3N / methanol / 2 h / Heating 3.1: pyridine / CH2Cl2 / 20 °C 4.1: LiBr / acetone / Heating 5.1: sodium sulfide nonahydrate / ethanol / Heating 6.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 6.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 7.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1.1: Et3N / methanol / 2 h / Heating 2.1: pyridine / CH2Cl2 / 20 °C 3.1: LiBr / acetone / Heating 4.1: sodium sulfide nonahydrate / ethanol / Heating 5.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 5.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 6.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1.1: pyridine / CH2Cl2 / 20 °C 2.1: LiBr / acetone / Heating 3.1: sodium sulfide nonahydrate / ethanol / Heating 4.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 4.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 5.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1.1: LiBr / acetone / Heating 2.1: sodium sulfide nonahydrate / ethanol / Heating 3.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 3.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 4.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme

1.1: N-chlorosuccinimide / CCl4 / 3 h / Heating 1.2: 20 percent / m-chloroperbenzoic acid / CH2Cl2 / 18 h / 20 °C 2.1: 66 percent / potassium tert-butoxide / tetrahydrofuran; dimethylsulfoxide / 0.17 h / 20 °C View Scheme