2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 24 h; Heating;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 14 h; Heating;

1.1: copper(l) iodide / tetrahydrofuran / 0.67 h / -30 °C / |Inert atmosphere 1.2: 0.17 h / |Inert atmosphere 2.1: Dess-Martin periodane / dichloromethane / 1 h / 20 °C / |Inert atmosphere 3.1: tetrahydrofuran / 0 °C / |Inert atmosphere 4.1: potassium hydride; 18-crown-6 ether / tetrahydrofuran / 2.5 h / 0 - 20 °C / |Inert atmosphere View Scheme

1: tetrahydrofuran / 0 °C / |Inert atmosphere 2: potassium hydride; 18-crown-6 ether / tetrahydrofuran / 2.5 h / 0 - 20 °C / |Inert atmosphere View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in benzene 14 h; Heating; Yield given;

1: 100 mg / lithium, ammonia / ethanol / 1.5 h 2: 1.) pyridine, 2.) t-BuOK / 1.) RT, 5 d, 2.) t-BuOH, 40 deg C, 1 h View Scheme

1: tetrahydrofuran / -78 - 0 °C / Inert atmosphere 2: tetrahydrofuran / 0 - 50 °C / Inert atmosphere 3: potassium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere View Scheme

pyridine; potassium tert-butylate 1.) RT, 5 d, 2.) t-BuOH, 40 deg C, 1 h; Yield given. Multistep reaction;