water; 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate) in acetonitrile T=20°C; 5 h;

camphor-10-sulfonic acid in dichloromethane T=20°C; 2 h;

1: With 9-bora-bicyclo[3.3.1]nonane in tetrahydrofuran T=20°C; 2: With sodium hydroxide; dihydrogen peroxide in tetrahydrofuran T=20°C; 3 h;

1.1: 93 percent / TsOH / toluene / 3 h / Heating 2.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 20 °C 2.2: 78 percent / NaOH; H2O2 / tetrahydrofuran / 3 h / 20 °C View Scheme