1: With pyridine; 4,4'-diaminostilbene-2,2'-disulfonic acid in toluene T=20°C; 2 h; 2: in toluene T=50°C; 5 h;

1: 30 percent / LiN3 / ethanol / 2 h / Heating 2: 65 percent / DAST / benzene / 2 h / Ambient temperature View Scheme

1: 1.) pyridine / 1.) a) 0 deg C, overnight, b) 70 deg C, 3 h, 2.) a) 0 deg C, 1 h, b) RT, overnight 2: 95 percent / 1 N NaOH / ethanol / 3 h / 60 °C 3: 30 percent / LiN3 / ethanol / 2 h / Heating 4: 65 percent / DAST / benzene / 2 h / Ambient temperature View Scheme

1: 95 percent / 1 N NaOH / ethanol / 3 h / 60 °C 2: 30 percent / LiN3 / ethanol / 2 h / Heating 3: 65 percent / DAST / benzene / 2 h / Ambient temperature View Scheme

1: 1.) pyridine / 1.) a) 0 deg C, overnight, b) 70 deg C, 3 h, 2.) a) 0 deg C, 1 h, b) RT, overnight 2: 95 percent / 1 N NaOH / ethanol / 3 h / 60 °C 3: 30 percent / LiN3 / ethanol / 2 h / Heating 4: 65 percent / DAST / benzene / 2 h / Ambient temperature View Scheme

1.1: chlorotrimethylsilane; pyridine / various solvent(s) / Heating 1.2: trimethylsilil trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h 2.1: 1.52 g / NaOCH3 / methanol / 1 h 3.1: pyridine / 7 h / 65 °C 3.2: 92.7 percent / pyridine / 48 h / 20 °C 4.1: 81 percent / trifluoromethanesulfonyl chloride; DMAP / CH2Cl2 / 2 h 5.1: 88.1 percent / NaOH / ethanol; H2O / 4 h / 20 °C 6.1: DAST; pyridine / toluene / 2 h / 20 °C 6.2: 90 percent / toluene / 5 h / 50 °C View Scheme

1.1: chlorotrimethylsilane; pyridine / various solvent(s) / Heating 1.2: trimethylsilil trifluoromethanesulfonate / 1,2-dichloro-ethane / 5 h 2.1: 1.52 g / NaOCH3 / methanol / 1 h 3.1: pyridine / 7 h / 65 °C 3.2: 92.7 percent / pyridine / 48 h / 20 °C 4.1: 81 percent / trifluoromethanesulfonyl chloride; DMAP / CH2Cl2 / 2 h 5.1: 88.1 percent / NaOH / ethanol; H2O / 4 h / 20 °C 6.1: DAST; pyridine / toluene / 2 h / 20 °C 6.2: 90 percent / toluene / 5 h / 50 °C View Scheme

1.1: pyridine / 7 h / 65 °C 1.2: 92.7 percent / pyridine / 48 h / 20 °C 2.1: 81 percent / trifluoromethanesulfonyl chloride; DMAP / CH2Cl2 / 2 h 3.1: 88.1 percent / NaOH / ethanol; H2O / 4 h / 20 °C 4.1: DAST; pyridine / toluene / 2 h / 20 °C 4.2: 90 percent / toluene / 5 h / 50 °C View Scheme

1.1: 1.52 g / NaOCH3 / methanol / 1 h 2.1: pyridine / 7 h / 65 °C 2.2: 92.7 percent / pyridine / 48 h / 20 °C 3.1: 81 percent / trifluoromethanesulfonyl chloride; DMAP / CH2Cl2 / 2 h 4.1: 88.1 percent / NaOH / ethanol; H2O / 4 h / 20 °C 5.1: DAST; pyridine / toluene / 2 h / 20 °C 5.2: 90 percent / toluene / 5 h / 50 °C View Scheme

1.1: 88.1 percent / NaOH / ethanol; H2O / 4 h / 20 °C 2.1: DAST; pyridine / toluene / 2 h / 20 °C 2.2: 90 percent / toluene / 5 h / 50 °C View Scheme