sodium hydroxide; N-hexadecyl-N,N,N-trimethylammonium bromide in dichloromethane 15 h; Ambient temperature;

sodium hydroxide; N-hexadecyl-N,N,N-trimethylammonium bromide in dichloromethane 15 h; Ambient temperature;

2,3-dicyano-5,6-dichloro-p-benzoquinone in toluene T=110°C; 3 h; Inert atmosphere;

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 3 h / 110 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 - 20 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere 4: tetrahydrofuran / 0.17 h / 80 °C / Inert atmosphere; Microwave irradiation 5: 6.5 h / 25 °C View Scheme

1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 3 h / 110 °C / Inert atmosphere 2: potassium carbonate / acetone / 0 - 20 °C / Inert atmosphere 3: sodium tetrahydroborate / methanol / 0 - 20 °C / Inert atmosphere View Scheme