samarium diiodide; 2-propanethiol in tetrahydrofuran T=25°C; 1 h;

1.1: O3 / CH2Cl2 / -78 - 20 °C 1.2: Me2S / CH2Cl2 / 5 h / 20 °C 1.3: 589 mg / Ph3P / CH2Cl2 / 5 h / 20 °C 2.1: 99 percent / i-PrSH; SmI2 / tetrahydrofuran / 1 h / 25 °C View Scheme

1.1: p-TsOH / benzene / Heating 2.1: O3 / CH2Cl2 / -78 - 20 °C 2.2: Me2S / CH2Cl2 / 5 h / 20 °C 2.3: 589 mg / Ph3P / CH2Cl2 / 5 h / 20 °C 3.1: 99 percent / i-PrSH; SmI2 / tetrahydrofuran / 1 h / 25 °C View Scheme

1.1: diethyl ether / 25 °C 2.1: p-TsOH / benzene / Heating 3.1: O3 / CH2Cl2 / -78 - 20 °C 3.2: Me2S / CH2Cl2 / 5 h / 20 °C 3.3: 589 mg / Ph3P / CH2Cl2 / 5 h / 20 °C 4.1: 99 percent / i-PrSH; SmI2 / tetrahydrofuran / 1 h / 25 °C View Scheme

1.1: diethyl ether / 25 °C 2.1: p-TsOH / benzene / Heating 3.1: O3 / CH2Cl2 / -78 - 20 °C 3.2: Me2S / CH2Cl2 / 5 h / 20 °C 3.3: 589 mg / Ph3P / CH2Cl2 / 5 h / 20 °C 4.1: 99 percent / i-PrSH; SmI2 / tetrahydrofuran / 1 h / 25 °C View Scheme

sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate; Triton X-100 2) CH2Cl2, 0 deg C, 30 min; Yield given. Multistep reaction;