ruthenium trichloride; sodium periodate in tetrachloromethane; water; acetonitrile 6 h;

1: 69 percent / oxalyl chloride; dimethyl sulfoxide / CH2Cl2 / 0.33 h / -78 °C 2: 76 mg / ruthenium(III) chloride hydrate; NaIO4 / CCl4; acetonitrile; H2O / 6 h View Scheme

1: 162 mg / LAH; aluminum chloride / tetrahydrofuran / 0 deg C, 30 min; reflux, 2 h 2: 69 percent / oxalyl chloride; dimethyl sulfoxide / CH2Cl2 / 0.33 h / -78 °C 3: 76 mg / ruthenium(III) chloride hydrate; NaIO4 / CCl4; acetonitrile; H2O / 6 h View Scheme

1: With boron tribromide in dichloromethane T=-78 - -40°C; 0.666667 h; 2: With hydrogenchloride in water 1 h; Heating;