3-ethylpentan-3-yl thiol; oxygen in diethyl ether Irradiation;

1: 60 percent / DMAP / diethyl ether 2: 55 percent / 1,1-diethylpropanethiol, O2 / diethyl ether / Irradiation View Scheme

1: dimethylsulfoxide / 3 h / 100 °C 2: 83 percent / KOH, H2O2 3: 92 percent / oxalyl chloride, DMF / benzene / 4 h / Ambient temperature 4: 60 percent / DMAP / diethyl ether 5: 55 percent / 1,1-diethylpropanethiol, O2 / diethyl ether / Irradiation View Scheme

1: 92 percent / oxalyl chloride, DMF / benzene / 4 h / Ambient temperature 2: 60 percent / DMAP / diethyl ether 3: 55 percent / 1,1-diethylpropanethiol, O2 / diethyl ether / Irradiation View Scheme

1: 83 percent / KOH, H2O2 2: 92 percent / oxalyl chloride, DMF / benzene / 4 h / Ambient temperature 3: 60 percent / DMAP / diethyl ether 4: 55 percent / 1,1-diethylpropanethiol, O2 / diethyl ether / Irradiation View Scheme

1: 48 percent / chromic acid / diethyl ether 2: 75 percent / ethanol / 40 - 50 °C 3: sodium cyanoborohydride, toluene-p-sulphonic acid / tetrahydrofuran / 4 h / pH 3.5 4: 30percent aq. hydrogen peroxide, sodium peroxide / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 75 percent / ethanol / 40 - 50 °C 2: sodium cyanoborohydride, toluene-p-sulphonic acid / tetrahydrofuran / 4 h / pH 3.5 3: 30percent aq. hydrogen peroxide, sodium peroxide / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 87 percent / ethanol / 40 - 50 °C 2: sodium cyanoborohydride / CH2Cl2; methanol / 2 h / 0 °C 3: 30percent aq. hydrogen peroxide, sodium peroxide / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 59 percent / potassium dichromate, conc. sulphuric acid / H2O; diethyl ether / 0.5 h / -1 °C 2: 87 percent / ethanol / 40 - 50 °C 3: sodium cyanoborohydride / CH2Cl2; methanol / 2 h / 0 °C 4: 30percent aq. hydrogen peroxide, sodium peroxide / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 58 percent / potassium hydroxide / H2O / 5 h / Heating 2: 59 percent / potassium dichromate, conc. sulphuric acid / H2O; diethyl ether / 0.5 h / -1 °C 3: 87 percent / ethanol / 40 - 50 °C 4: sodium cyanoborohydride / CH2Cl2; methanol / 2 h / 0 °C 5: 30percent aq. hydrogen peroxide, sodium peroxide / tetrahydrofuran / 24 h / Ambient temperature View Scheme