tetrabutyl ammonium fluoride in tetrahydrofuran T=20°C; 1 h;

1: 95 percent / imidazole / dimethylformamide / 1.2 h / -30 - -20 °C 2: 97 percent / triphenylphosphine; hydrazoic acid; diethyl azodicarboxylate / tetrahydrofuran; benzene / 2 h / 20 °C 3: 70 percent / propane-1,3-dithiol; Et3N / methanol / 12 h / 20 °C 4: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: 95 percent / tetrahydrofuran / 0.67 h / -50 °C 2.1: B2H6 / tetrahydrofuran / 20 h / 0 °C 2.2: 82 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 3.1: 95 percent / imidazole / dimethylformamide / 1.2 h / -30 - -20 °C 4.1: 97 percent / triphenylphosphine; hydrazoic acid; diethyl azodicarboxylate / tetrahydrofuran; benzene / 2 h / 20 °C 5.1: 70 percent / propane-1,3-dithiol; Et3N / methanol / 12 h / 20 °C 6.1: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 97 percent / triphenylphosphine; hydrazoic acid; diethyl azodicarboxylate / tetrahydrofuran; benzene / 2 h / 20 °C 2: 70 percent / propane-1,3-dithiol; Et3N / methanol / 12 h / 20 °C 3: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 70 percent / propane-1,3-dithiol; Et3N / methanol / 12 h / 20 °C 2: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme

1.1: B2H6 / tetrahydrofuran / 20 h / 0 °C 1.2: 82 percent / aq. NaOH; H2O2 / 0.5 h / 0 °C 2.1: 95 percent / imidazole / dimethylformamide / 1.2 h / -30 - -20 °C 3.1: 97 percent / triphenylphosphine; hydrazoic acid; diethyl azodicarboxylate / tetrahydrofuran; benzene / 2 h / 20 °C 4.1: 70 percent / propane-1,3-dithiol; Et3N / methanol / 12 h / 20 °C 5.1: 82 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1 h / 20 °C View Scheme