2,2'-azo-bisisobutyronitrile in o-di-fluorobenzene 3 h; Heating;

2,2'-azo-bisisobutyronitrile in o-di-fluorobenzene 3 h; Heating;

in decalin 2 h; Heating;

tert.-butylnitrite; trimethylsilylazide in acetonitrile T=0 - 20°C;

1: 40 percent / ZnCl2 / xylene / 8 h / Heating 2: 1.) aq. HCl, NaNO2, 2.) NaN3 / 1.) -5 to 0 deg C, 2.) 1 h View Scheme

1.1: tetrahydrofuran / 72 h / 20 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 2.2: 0 °C / Inert atmosphere; Reflux 3.1: acetyl chloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere 4.1: boron trifluoride diethyl etherate / anhydrous xylene / 16 h / Inert atmosphere; Reflux 5.1: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 0 - 20 °C View Scheme

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere 1.2: 0 °C / Inert atmosphere; Reflux 2.1: acetyl chloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere 3.1: boron trifluoride diethyl etherate / anhydrous xylene / 16 h / Inert atmosphere; Reflux 4.1: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 0 - 20 °C View Scheme

1: acetyl chloride / methanol / 2 h / 0 - 20 °C / Inert atmosphere 2: boron trifluoride diethyl etherate / anhydrous xylene / 16 h / Inert atmosphere; Reflux 3: tert.-butylnitrite; trimethylsilylazide / acetonitrile / 0 - 20 °C View Scheme

2-methyl-2-iodopropane in dichloromethane T=20°C; 18 h; Inert atmosphere;

sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide 1) acetone, H2O 2) THF, H2O; Yield given. Multistep reaction;