1: 1-hydroxyindan With peracetic acid; C9H17NO5S(1-)*C12H11IN(1+); acetic acid in hexafluoroisopropyl alcohol T=20°C; 12 h; 2: (2,4-dinitro-phenyl)-hydrazine With sulfuric acid in diethyl ether; ethanol; water

1: (diacetoxyiodo)benzene / RuCl3 / acetonitrile; H2O / 1.5 h / 20 °C 2: H2SO4 / acetonitrile; H2O; ethanol View Scheme

1: 94 percent / Br2; 1,2-bis(diphenylphosphino)ethane / CH2Cl2 / -15 - 15 °C 2: fuming NH2NH2 / 0.5 h / sonication View Scheme

sodium tetrahydroborate; trifluorormethanesulfonic acid 1.) CH2Cl2, 2.) MeOH; Yield given. Multistep reaction. Yields of byproduct given;

C36H40O20S4 in water T=60°C; 24 h;

pyridine

1.1: thionyl chloride / dichloromethane / 9 h / 0 °C / |Inert atmosphere; |Reflux 2.1: dimethyl sulfoxide / 2 h / 140 °C / |Inert atmosphere 3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 21 h / |Inert atmosphere; |Reflux 4.1: diisobutylaluminium hydride / toluene / 1.5 h / -78 °C / |Inert atmosphere 5.1: lithium diisopropyl amide / tetrahydrofuran / 0.5 h / -95 °C / |Inert atmosphere 5.2: -95 - -30 °C / |Inert atmosphere 5.3: 1.5 h / -30 - 0 °C / |Inert atmosphere 6.1: zinc / N,N-dimethyl-formamide / 2 h / 20 °C / |Inert atmosphere 7.1: indium tribromide / 1,2-dichloro-ethane / 0.5 h / 20 °C / |Inert atmosphere; |Glovebox 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / 1,2-dichloro-ethane / 1.5 h / |Inert atmosphere; |Reflux; |Glovebox View Scheme