hydroxylamine hydrochloride; sodium hydroxide in water T=20°C; Aza-Michael addition; pH=12; 4 h; stereoselective reaction;

1.1: tetrahydrofuran / -15 - 25 °C / Inert atmosphere 1.2: 0 - 5 °C 2.1: potassium carbonate / dimethyl sulfoxide / 0.25 h / 25 °C 2.2: 1 h / 25 °C 3.1: tri-n-butyl-tin hydride / 2,2'-azo-bisisobutyronitrile / toluene / 10 h / Reflux 3.2: 20 °C 4.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 4.2: pH 1 5.1: di-isopropyl ether / 6 h / 20 - 75 °C 6.1: hydrogenchloride / water; tert-butyl methyl ether / 0.5 h / 20 - 25 °C 7.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 8.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 9.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 9.2: 0.5 h / 0 - 5 °C View Scheme

1.1: tetrahydrofuran / -15 - 25 °C / Inert atmosphere 1.2: 0 - 5 °C 2.1: potassium carbonate / dimethyl sulfoxide / 0.25 h / 25 °C 2.2: 1 h / 25 °C 3.1: tri-n-butyl-tin hydride / 2,2'-azo-bisisobutyronitrile / toluene / 10 h / Reflux 3.2: 20 °C 4.1: sodium hydroxide / ethylene glycol / 4 h / 170 - 180 °C 4.2: pH 1 5.1: thionyl chloride / toluene / 3 h / 75 - 80 °C 6.1: sodium carbonate / toluene; water / 1 h / 0 - 5 °C 7.1: dimethylsulfide borane complex / tetrahydrofuran / 3 h / 20 - 80 °C / Inert atmosphere 7.2: 0.5 h / 0 - 5 °C 8.1: hydrogen bromide / water / 3 h / 90 - 100 °C 9.1: (2S,3S)-(+)-di-O-benzoyl tartaric acid / isobutyl methylketone; methanol / 25 °C 9.2: pH 8 View Scheme

polyacrylonitrile fiber functionalized with N,N-dimethyl-1,3-propanediamine in ethanol T=20°C; Knoevenagel condensation; 1 h;

2,2-Dimethyl-[1,3]dioxane-4,6-dione; water T=80°C; Knoevenagel condensation; 1.5 h;

air; silica gel T=90°C; 0.5 h; neat (no solvent);