1: 73 percent / diisopropylazodicarboxylate, tributylphosphine 2: 78 percent / LHMDS / tetrahydrofuran / -78 °C 3: 95 percent / MsN3, Et3N 4: 62 percent / 5 mol percent of rhodium pivalate <Rh2(piv)4> / benzene / 1 h / Heating 5: 1.) O3, 2.) DMS / 1.) CH2Cl2, MeOH 6: tetrahydrofuran / Ambient temperature 7: 100 percent / TFA 8: 1.) diphenyl phosphorazidate, Et3N, 2.) aq. HCl / 1.) toluene, reflux, 2.) reflux, 2 h 9: 49 percent / NaOMe / methanol / Ambient temperature 10: 95 percent / tetrahydrofuran / Ambient temperature View Scheme

aluminium trichloride in chlorobenzene 0.5 h; Heating;

1: 93 percent / pyridine 2: 94 percent / AlCl3 / chlorobenzene / 0.5 h / Heating View Scheme

chlorine in tetrachloromethane 18 h;

1: 2.075 g / HNO3 / acetic acid; acetic anhydride / 96 h / 0 °C 2: 0.086 g / Zn, SnCl2, HCl / ethanol / 0.17 h / Heating 3: 1.) NaNO2 2.) CuCl, HCl / 1.) water, 0 deg C, 0.5 h 2.) 12 h View Scheme

2: 0.865 g / Cl2 / CCl4 / 18 h View Scheme

1: 0.086 g / Zn, SnCl2, HCl / ethanol / 0.17 h / Heating 2: 1.) NaNO2 2.) CuCl, HCl / 1.) water, 0 deg C, 0.5 h 2.) 12 h View Scheme

hydrogenchloride; copper(l) chloride; sodium nitrite 1.) water, 0 deg C, 0.5 h 2.) 12 h; Yield given. Multistep reaction;

aluminium trichloride; nitrobenzene