1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 2: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 3: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 4: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 2: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: imidazole / CH2Cl2 / 0.17 h / 0 °C 1.2: 98 percent / CH2Cl2 / 4 h / 23 °C 2.1: 56 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 12 h / 80 °C 3.1: 90 percent / (+)-DET; Ti(OiPr)4; TBHP / diethyl ether / 12 h / -30 °C 4.1: 90 percent / SO3*Py; Et3N / dimethylsulfoxide / 1 h 5.1: 80 percent / NaHMDS / 0 °C 6.1: 98 percent / nBu4NF / tetrahydrofuran / 6 h / 23 °C 7.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 8.1: 91 percent / iPr2NEt; tetrabutylammonium iodide / dimethylformamide / 4 h / 80 °C 9.1: LDA / tetrahydrofuran / 0.08 h / -78 °C 9.2: 81 percent / tetrahydrofuran / 0.08 h / -78 °C 10.1: 94 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / 120 °C 11.1: aq. H2O2 / toluene / 3 h 12.1: toluene / 1 h / 80 °C 13.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 14.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 15.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: H2O2; (CF3)2CHOH / 3 h / 23 °C 1.2: 92 percent / toluene / 1 h / 80 °C 2.1: 87 percent / Grubb's catalyst / toluene / 0.17 h / 120 °C 3.1: 68 percent / SOCl2 / diethyl ether / 0 °C 4.1: 74 percent / aq. HCl / dioxane / 3 h / 23 °C 5.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: MgClO4; H2SO4 / CHCl3 / 2 h / 25 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 2.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 3.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 4.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 5.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 5.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 6.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 7.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 1.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 2.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 3.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 4.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 4.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 5.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 6.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

Na2B4O7 in tetrahydrofuran; methanol 24 h; Ambient temperature;

1.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 2.1: 91 percent / EtiPr2N; TBAI / dimethylformamide / 3 h / 80 °C 3.1: LDA / tetrahydrofuran / -78 °C 3.2: 81 percent / tetrahydrofuran / cooling 4.1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 5.1: 249 mg / toluene / 1 h / 80 °C 6.1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 7.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 8.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 9.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 91 percent / EtiPr2N; TBAI / dimethylformamide / 3 h / 80 °C 2.1: LDA / tetrahydrofuran / -78 °C 2.2: 81 percent / tetrahydrofuran / cooling 3.1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 4.1: 249 mg / toluene / 1 h / 80 °C 5.1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 6.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 7.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 8.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: 98 percent / nBu4NF / tetrahydrofuran / 6 h / 23 °C 2.1: 84 percent / tris(3-chlorophenyl)phosphine; DIAD / toluene / 3 h / 23 °C 3.1: 91 percent / EtiPr2N; TBAI / dimethylformamide / 3 h / 80 °C 4.1: LDA / tetrahydrofuran / -78 °C 4.2: 81 percent / tetrahydrofuran / cooling 5.1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 6.1: 249 mg / toluene / 1 h / 80 °C 7.1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 8.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 9.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 10.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme