iodine in water T=20°C; 2 h;

iodine; silver trifluoromethanesulfonate in acetonitrile T=20°C; 1 h;

1.1: lithium / diethyl ether / 0.33 h / 20 °C / Inert atmosphere 1.2: 1 h / 20 °C / Inert atmosphere 2.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 3.1: iodine; silver trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C View Scheme

1.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 2.1: lithium / diethyl ether / 0.33 h / 20 °C / Inert atmosphere 2.2: 1 h / 20 °C / Inert atmosphere 3.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 4.1: iodine; silver trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C View Scheme

1.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 1.2: 120 - 215 °C 2.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 3.1: lithium / diethyl ether / 0.33 h / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C / Inert atmosphere 4.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 5.1: iodine; silver trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C View Scheme

1.1: AlCl3, aluminium chloride / tetrachloroethane, 1,1,2,2- 2.1: hydrazine hydrate / diethylene glycol / 0.5 h / 20 °C 2.2: 120 - 215 °C 3.1: methanesulfonic acid / 0.5 h / 90 °C / Inert atmosphere 4.1: lithium / diethyl ether / 0.33 h / 20 °C / Inert atmosphere 4.2: 1 h / 20 °C / Inert atmosphere 5.1: toluene-4-sulfonic acid / benzene / 2 h / Reflux 6.1: iodine; silver trifluoromethanesulfonate / acetonitrile / 1 h / 20 °C View Scheme

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / Reflux 2: palladium diacetate; CsO2CCMe3; bis(1,1-diphenylphosphino)methane / N,N-dimethyl-formamide / 12 h / 110 °C / Inert atmosphere View Scheme

2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene Reflux;