1: N-(heptyl)hydroxylamine-O-sulfonic acid With Schwartz's reagent in tetrahydrofuran T=25°C; 2: oct-1-ene in tetrahydrofuran T=80°C; 0.5 h;

1: T=25°C; 0.166667 h; 2: With sodium tetrahydroborate; boric acid T=25°C; 0.5 h;

T=160°C; 4 h; Inert atmosphere;

1.1: sodium hydroxide; hydroxylamine hydrochloride / water; ethanol / 2 h / 0 - 70 °C 2.1: hydrogenchloride; sodium cyanoborohydride / water; methanol / 0.01 h / -60 - 20 °C / pH < 3 3.1: chlorosulfonic acid / dichloromethane / 3.25 h / -78 - 20 °C / |Schlenk technique; |Inert atmosphere 4.1: Schwartz's reagent / tetrahydrofuran / 25 °C 4.2: 0.5 h / 80 °C View Scheme

1.1: hydrogenchloride; sodium cyanoborohydride / water; methanol / 0.01 h / -60 - 20 °C / pH < 3 2.1: chlorosulfonic acid / dichloromethane / 3.25 h / -78 - 20 °C / |Schlenk technique; |Inert atmosphere 3.1: Schwartz's reagent / tetrahydrofuran / 25 °C 3.2: 0.5 h / 80 °C View Scheme

1.1: chlorosulfonic acid / dichloromethane / 3.25 h / -78 - 20 °C / |Schlenk technique; |Inert atmosphere 2.1: Schwartz's reagent / tetrahydrofuran / 25 °C 2.2: 0.5 h / 80 °C View Scheme

dihydridotetrakis(triphenylphosphine)ruthenium(II) in neat (no solvent) Ruthenium catalyzed reaction of alcohols with amines at 155-180 deg C, 6-24 hr; Product distribution;

Al-Ni-Ti alloy T=165°C; P=38000 Torr; 4 h; Product distributionMechanism;