1: 1.) BuLi / 1.) THF, hexane, -15 deg C, 4 h, 2.) THF, hexane, RT, 1 h 2: 82 percent / cerium(IV) diammonium nitrate / acetonitrile; H2O / 0.33 h / 0 - 5 °C 3: 77 percent / HNO3, conc. H2SO4, Ac2O / 3 h / -5 °C View Scheme

1: 1.) BuLi / 1.) THF, hexane, -15 deg C, 4 h, 2.) THF, hexane, RT, 3 h 2: 79 percent / cerium(IV) diammonium nitrate / acetonitrile; H2O / 0.33 h / 0 - 5 °C View Scheme

ammonium cerium(IV) nitrate in water; acetonitrile T=0 - 5°C; Oxidation; 0.25 h;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '747939', constants.ctx, '0')">2,3-dicyano-5,6-dichloro-p-benzoquinone</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '969212', constants.ctx, '0')">benzene</a> <br />Dehydrogenation;&nbsp;0.5&nbsp;h;&nbsp;&nbsp;Heating;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 4 steps<br /> </b>1: SeO₂; aq. H₂O₂ / CH₂Cl₂ / 36 h / 20 &deg;C<br />2: KOH / methanol<br />3: 85 percent / aq. KOH / 8 h / 0 - 5 &deg;C<br />4: 75 percent / DDQ / benzene / 0.5 h / Heating<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: acetic acid; dihydrogen peroxide / 1 h / 75 &deg;C<br />2: quinoline; chromium copper oxide / 2 h / |Reflux<br />3: tetrabutylammomium bromide; potassium hydroxide; sodium dithionite / tetrahydrofuran / |Inert atmosphere<br /> <br /> &nbsp;