1: trimethylaluminum; (5E,9E,13E,17E,21E)-6,10,14,18,22,26-Hexamethyl-heptacosa-5,9,13,17,21,25-hexaen-1-yne With zirconocene dichloride in hexane; 1,2-dichloro-ethane Metallation; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With NiCl2((PPh3)P)2; n-butyllithium in tetrahydrofuran; hexane Alkylation;

1: trimethylaluminum; (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne With zirconocene dichloride in 1,2-dichloro-ethane T=23°C; 1 h; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With n-butyllithium; Cl2Ni(PPh)2; triphenylphosphine in tetrahydrofuran T=23°C; 1 h; Further stages.;

1: With Ni(PPh3)2.2THF in tetrahydrofuran; hexane T=20°C; 4 h; light absence; 2: With hydrogenchloride in tetrahydrofuran; hexane; water; ethyl acetate 0.166667 h; Product distribution / selectivity;

n-butyllithium; NiCl2((PPh3)P)2 in tetrahydrofuran T=-20°C; 1.5 h;

1: (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne With trimethylaluminum; zirconocene dichloride; iso-butylaluminoxane in dichloromethane; chlorobenzene T=-15°C; 14 h; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With n-butyllithium; NiCl2((PPh3)P)2 in tetrahydrofuran T=-20°C; 2 h; Product distribution / selectivity;

1: trimethylaluminum; (5E,9E,13E,17E,21E,25E)-6,10,14,18,22,26,30-Heptamethyl-hentriaconta-5,9,13,17,21,25,29-heptaen-1-yne With zirconocene dichloride in hexane; 1,2-dichloro-ethane carboalumination; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With NiCl2((PPh3)P)2; n-butyllithium in tetrahydrofuran; hexane Condensation;

n-butyllithium; zirconocene dichloride; triphenylphosphine; nickel dichloride 1.) ClCH2CH2Cl, 0 deg C, 2.) THF, hexane. -78 deg C, 30 min, -78 deg C to 0 deg C, 1.75 h; Yield given. Multistep reaction;

1: trimethylaluminum; (5E,9E)-6,10,14-trimethylpentadeca-5,9,13-trien-1-yne With methyl aluminoxane; rac-ethylenebis(1-indenyl)zirconium(IV) chloride in toluene T=20°C; Negishi carboalumination; 8 h; 2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With NiCl2((PPh3)P)2; n-butyllithium in tetrahydrofuran T=-20°C; 2 h;