1: tetrabutylammonium bromide / tetrahydrofuran / 4 h / 20 °C 2: tetrabutylammonium fluoride / tetrahydrofuran / 4 h / 20 °C View Scheme

tetrabutyl ammonium fluoride in dimethyl sulfoxide T=20°C; 4 h; Product distribution; Further Variations:ReagentsSolvents;

1: p-TolSO3H / benzene / Heating 2: 86 percent / NaBH3CN / methanol / 3 h / Ambient temperature; Irradiation View Scheme

tetrabutylammomium bromide in tetrahydrofuran T=20°C; 4 h;

1: 1.) p-toluene-sulfonic acid, 2.) NaI / 1.) THF, RT, 1 h, 2.) RT, 24 h, acetone 2: 48 percent / n-BuLi, diisopropylamine / tetrahydrofuran; hexane / -78 degC, 30 min and RT, 4 h 3: 1.) O2, 2.) p-toluenesulfonic acid / 1.) Sensitox / 1.) CH2Cl2, 30 min, irradiation, 2.) benzene, 24 h, reflux View Scheme