1: With ammonia; lithium in tetrahydrofuran; 1,1-dimethylpropan-1-ol T=-33°C; 10 h; 2: With ammonium chloride in tetrahydrofuran; pentanes; 1,1-dimethylpropan-1-ol; water; isoprene

hydrazine Wolff-Kishner Reduction; Heating / reflux;

in toluene Cope rearrangement; 2 h; Heating;

1.1: bis(benzonitrile)palladium(II) dichloride / toluene / 1 h / Reflux; Inert atmosphere 2.1: pyridine; potassium tert-butylate / 0.08 h / Inert atmosphere; Reflux 2.2: 0 - 20 °C / Inert atmosphere 3.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran; mineral oil / 0 - 20 °C 3.2: 0.25 h / Inert atmosphere; Reflux View Scheme

1.1: pyridine; potassium tert-butylate / 0.08 h / Inert atmosphere; Reflux 1.2: 0 - 20 °C / Inert atmosphere 2.1: carbon disulfide; sodium hydride; methyl iodide / tetrahydrofuran; mineral oil / 0 - 20 °C 2.2: 0.25 h / Inert atmosphere; Reflux View Scheme

pyridine; trichlorophosphate

T=200°C; Cope rearrangement;

N,N-dimethyl-aniline

lithium; ethylenediamine