2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane; water T=20°C; 1.5 h;

1.1: 85 percent / PPh3 / CH2Cl2 / 7 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 2.2: 98 percent / tetrahydrofuran; hexane / -78 - 20 °C 3.1: triethylamine; sulfur trioxide pyridine complex; DMSO / CH2Cl2 / 19 h / 20 °C 4.1: magnesium / tetrahydrofuran / 1.5 h / 0 °C 4.2: 64 percent / tetrahydrofuran / 2 h / 0 °C 5.1: 97 percent / pyridine / CH2Cl2 / 1 h / 0 °C 6.1: 99 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1.5 h / 20 °C View Scheme

1: 97 percent / pyridine / CH2Cl2 / 1 h / 0 °C 2: 99 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1.5 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C 1.2: 98 percent / tetrahydrofuran; hexane / -78 - 20 °C 2.1: triethylamine; sulfur trioxide pyridine complex; DMSO / CH2Cl2 / 19 h / 20 °C 3.1: magnesium / tetrahydrofuran / 1.5 h / 0 °C 3.2: 64 percent / tetrahydrofuran / 2 h / 0 °C 4.1: 97 percent / pyridine / CH2Cl2 / 1 h / 0 °C 5.1: 99 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1.5 h / 20 °C View Scheme

1.1: triethylamine; sulfur trioxide pyridine complex; DMSO / CH2Cl2 / 19 h / 20 °C 2.1: magnesium / tetrahydrofuran / 1.5 h / 0 °C 2.2: 64 percent / tetrahydrofuran / 2 h / 0 °C 3.1: 97 percent / pyridine / CH2Cl2 / 1 h / 0 °C 4.1: 99 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH2Cl2; H2O / 1.5 h / 20 °C View Scheme