1: With N-(diphenylmethylene)amine; sodium t-butanolate; tris-(dibenzylideneacetone)dipalladium(0); 9,9-dimethyl-4,5-bis(diphenyl-phosphino)xanthene in toluene T=110°C; 12 h; 2: With hydrogenchloride in 1,4-dioxane T=20°C; 2 h; 3: With triethylamine T=20°C; 0.5 h;

palladium 10 on activated carbon; hydrogen in ethanol T=20°C; 4 h;

in tetrahydrofuran T=-78°C;

1: 71 percent / H2O2 / methanol / 1.) 0 deg C, 1 h, 2.) r.t., overnight 2: 1.) HBr, NaNO2, 2.) CuBr, HBr / 1.) H2O, 0-5 deg C, 20 min, then 15-20 deg C, 15 min 2.) H2O, r.t., 30 min View Scheme

hydrogen bromide; copper(I) bromide; sodium nitrite 1.) H2O, 0-5 deg C, 20 min, then 15-20 deg C, 15 min 2.) H2O, r.t., 30 min; Yield given. Multistep reaction. Yields of byproduct given;

1: 89 percent / glacial acetic acid / 0.5 h / Heating 2: 84 percent / lithium aluminum hydride / diethyl ether / 8 h / Heating 3: 89 percent / triethylamine / CH2Cl2 / 1 h / Ambient temperature 4: 26 percent / phosphorus oxychloride / 2 h / Heating 5: 78 percent / lithium aluminium hydride / tetrahydrofuran / 10 h / Heating View Scheme

1: Reflux; 2: With hydrazine hydrate in ethanol Reflux;