silica gel; pyridinium chlorochromate in dichloromethane T=20°C; 2 h;

iron tribromide in toluene T=80°C; Wagner-Meerwein Rearrangement; 14 h; Sealed tubeSchlenk techniqueInert atmosphere; chemoselective reaction;

1: ortho-dibromobenzene With isopropylmagnesium chloride lithium chloride complex in tetrahydrofuran T=-15°C; 3 h; 2: in tetrahydrofuran T=-20°C; 0.166667 h; 3: cyclohexane carboxylic acid chloride in tetrahydrofuran T=-10°C; 15 h; Further stages.;

1: sodium hexamethyldisilazane / |Inert atmosphere; |Schlenk technique 2: diisobutylaluminium hydride / |Inert atmosphere; |Schlenk technique 3: iron tribromide / toluene / 14 h / 80 °C / |Sealed tube; |Schlenk technique; |Inert atmosphere View Scheme

1: diisobutylaluminium hydride / |Inert atmosphere; |Schlenk technique 2: iron tribromide / toluene / 14 h / 80 °C / |Sealed tube; |Schlenk technique; |Inert atmosphere View Scheme

1: tetrahydrofuran / 2 h / -50 - 20 °C 2: pyridinium chlorochromate; silica gel / dichloromethane / 2 h / 20 °C View Scheme