1.1: LDA / tetrahydrofuran / -78 °C 1.2: 81 percent / tetrahydrofuran / cooling 2.1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 3.1: 249 mg / toluene / 1 h / 80 °C 4.1: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 5.1: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 6.1: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 7.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1: aq. H2O2 / various solvent(s) / 3 h / 23 °C 2: 249 mg / toluene / 1 h / 80 °C 3: 87 percent / PhCH=Ru{[(MeS)NCH2CH2N(MeS)]}(PCy3)Cl2 / toluene / 0.17 h / Heating 4: 68 percent / SO2Cl2 / diethyl ether / 1.5 h / 0 °C 5: 74 percent / aq. HCl / dioxane / 1 h / 0 - 23 °C 6: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: H2O2; (CF3)2CHOH / 3 h / 23 °C 1.2: 22 percent / toluene / 1 h / 80 °C 2.1: 68 percent / SOCl2 / diethyl ether / 0 °C 3.1: 74 percent / aq. HCl / dioxane / 3 h / 23 °C 4.1: 86 percent / K2CO3 / dimethylformamide / 1 h / 23 °C View Scheme

1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 - 25 °C 1.2: 82 percent / tetrahydrofuran / 0.17 h 2.1: 89 percent / TBAF 3.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 4.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 5.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 6.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 7.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 7.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 8.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 9.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: 90 percent / SO3*pyridine; Et3N; DMSO / CH2Cl2 / 0 - 25 °C 2.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 - 25 °C 2.2: 82 percent / tetrahydrofuran / 0.17 h 3.1: 89 percent / TBAF 4.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 5.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 6.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 7.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 8.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 8.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 9.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 10.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: POCl3 / 0.33 h / 25 °C 1.2: 93 percent / 2 h / 25 - 75 °C 2.1: 96 percent / BBr3 / CH2Cl2 / 20 h / 25 °C 3.1: 97 percent / imidazole / CH2Cl2; tetrahydrofuran / 12 h / 25 °C 4.1: 100 percent / NaOCl2; sulfamic acid / tetrahydrofuran; H2O; dimethylsulfoxide / 0.5 h / 0 °C 5.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 6.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 6.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 7.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 8.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 9.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 9.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 10.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 11.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: 96 percent / BBr3 / CH2Cl2 / 20 h / 25 °C 2.1: 97 percent / imidazole / CH2Cl2; tetrahydrofuran / 12 h / 25 °C 3.1: 100 percent / NaOCl2; sulfamic acid / tetrahydrofuran; H2O; dimethylsulfoxide / 0.5 h / 0 °C 4.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 5.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 5.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 6.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 7.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 8.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 8.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 9.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 10.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: 97 percent / imidazole / CH2Cl2; tetrahydrofuran / 12 h / 25 °C 2.1: 100 percent / NaOCl2; sulfamic acid / tetrahydrofuran; H2O; dimethylsulfoxide / 0.5 h / 0 °C 3.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 4.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 5.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 6.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 7.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 7.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 8.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 9.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: 100 percent / NaOCl2; sulfamic acid / tetrahydrofuran; H2O; dimethylsulfoxide / 0.5 h / 0 °C 2.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -20 °C 3.2: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C 4.1: 88 percent / imidazole / dimethylformamide / 3 h / 25 °C 5.1: 60 percent / (PCy)3Cl2Ru=CHPh(1,3-di-Mes-imidazolidine-2-yl) / CH2Cl2 / 2 h / 42 °C 6.1: mCPBA / CH2Cl2 / 0.08 h / -10 °C 6.2: Ac2O; Et3N / H2O; tetrahydrofuran / 12 h / 60 °C 7.1: 58 percent / NaHCO3 / methanol; H2O / 24 h 8.1: 58 percent / SO2Cl2 / diethyl ether / 0 °C View Scheme

1.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 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