in 1,4-dioxane 8 h; Reflux;

triethylamine in benzene Substitution; dehydrochlorination; Heating;

in toluene T=0°C;

in THF-d8 (tetrahydrofuran-d8) T=20°C; Equilibrium constant; TimeSolvent;

1: 96 percent / sulfuric acid / 0.5 h / Heating 2: 94 percent / toluene / 0 °C View Scheme

in toluene 2 h; Heating;

chlorobenzene

1.1: tetrahydrofuran / 18 h / 60 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3.2: 20 h / 60 °C / Inert atmosphere 4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 44 h / 20 °C 5.1: sodium periodate / methanol; water / 0.5 h 6.1: tris-[2-carboxyethyl]-phosphine / water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 7.1: water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere View Scheme

pyridine

1.1: tetrahydrofuran / 18 h / 60 °C / Inert atmosphere 2.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 °C / Inert atmosphere 3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 3.2: 20 h / 60 °C / Inert atmosphere 4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 44 h / 20 °C 5.1: sodium periodate / methanol; water / 0.5 h 6.1: tris-[2-carboxyethyl]-phosphine / water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 7.1: water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 8.1: sulfuric acid; sodium nitrite / tetrahydrofuran; water / 1 h / 0 °C 8.2: 0 - 20 °C 9.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C View Scheme