1: 1-Chloro-3,3-dimethylbut-1-yne With n-butyllithium in n-heptane; toluene T=80°C; 2.5 h; 2: (E)-N-methyl N-naphthyl methylene-3-chloro-prop-2-en-1-amine With nickel dichloride in tetrahydrofuran; toluene T=50 - 95°C; 1 h; Product distribution / selectivity;

water; bis-(1,2-dimethylpropyl)borane; copper dichloride 1.) THF, -15 deg C, 30 min; 0-5 deg C, 30 min, 2.) HMPT, 0-5 deg C, 2 h; 20 deg C, 15 h; Yield given. Multistep reaction;

1: dimethylformamide; methanol 2: aq. HCl View Scheme