2,3-dicyano-5,6-dichloro-p-benzoquinone in dichloromethane T=20°C; 24 h;

1: toluene-4-sulfonic acid; lithium bromide / 24 h / Inert atmosphere; Reflux 2: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C / Inert atmosphere 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 24 h / 20 °C / Inert atmosphere View Scheme

1: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C / Inert atmosphere 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 24 h / 20 °C / Inert atmosphere View Scheme

1: dimethylsulfide borane complex / tetrahydrofuran / 1 h / Inert atmosphere; Reflux 2: toluene-4-sulfonic acid; lithium bromide / 24 h / Inert atmosphere; Reflux 3: trimethylsilyl trifluoromethanesulfonate / acetonitrile / 0 - 20 °C / Inert atmosphere 4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 24 h / 20 °C / Inert atmosphere View Scheme

Amberlyst 15 in methanol

toluene-4-sulfonic acid in dimethylsulfoxide-d6; chloroform-d1 T=30°C; half-time life;

trimethylsilyl bromide; tetrabutylammomium bromide in toluene T=80°C; 4 h;

hydrogenchloride in tetrahydrofuran 0.333333 h; Ambient temperature;