1: hex-1-yne With n-butyllithium in tetrahydrofuran; hexane T=-78 - 20°C; 2: 1-n-heptylbromide With sodium iodide in tetrahydrofuran 15 h; Heating;

1: hex-1-yne With n-butyllithium in tetrahydrofuran; hexane T=-78 - 20°C; 2: 1-heptylchloride With tetra-(n-butyl)ammonium iodide in tetrahydrofuran 60 h; Heating;

samarium diiodide; isopropyl alcohol; tetrakis(triphenylphosphine) palladium(0) in tetrahydrofuran T=40°C; 2 h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

1: 98 percent / potassium tert-butoxide / tetrahydrofuran / 1.5 h / -78 °C 2: 40 percent / cooper(II) acetylacetonate / tetrahydrofuran / 6 h 3: 1.) MCPBA, 2.) DABCO / 1.) chloroform, 2.) benzene, 95 deg C, 24 h View Scheme

1: 40 percent / cooper(II) acetylacetonate / tetrahydrofuran / 6 h 2: 1.) MCPBA, 2.) DABCO / 1.) chloroform, 2.) benzene, 95 deg C, 24 h View Scheme

1,4-diaza-bicyclo[2.2.2]octane; 3-chloro-benzenecarboperoxoic acid 1.) chloroform, 2.) benzene, 95 deg C, 24 h; Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts;