Synthesis of 2,6-Diphenylbarbarlane by Oxidation of Dipotassium 2,6-Diphenylbicyclo[3.3.1]nonadienediide with 1,2-Dibromoethane. – Preparative Reversed-Phase Liquid Chromatography of Hydrocarbons

The diphenylbicyclo[3.3.1]nonadiene 11 is deprotonated by butylpotassium to afford the black-red crystalline dipotassium diphenylbicyclo[3.3.1]nonadienediide 12. At low temperatures, 12 is oxidized in tetrahydrofuran solution by 1,2-dibromo-ethane yielding the diphenylbarbaralane 13 which is isolated in 57% yield on a 20-mmol scale after cyclic liquid chromatography on C18 reversed-phase silica gel with methanol. The packing procedure for suitable columns is also detailed.

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