copper; benzoyl chloride in N,N-dimethyl-formamide T=150°C; 0.5 h;

copper in N,N-dimethyl-formamide T=150°C;

para-xylene; copper in N,N-dimethyl-formamide T=150°C; 1 h; Further byproducts given;

isopropyl-benzene; copper in N,N-dimethyl-formamide T=150°C; 1 h; Further byproducts given;

1: copper(I) iodide / tetrahydrofuran 2: 2.5 percent / p-xylene, benzoyl chloride / dimethylformamide / 23 h / Heating View Scheme

para-xylene; benzoyl chloride in N,N-dimethyl-formamide 23 h; Heating;

carbon dioxide 1.) Pb cathode, -1.50 V, Et4NBF4, DMF, 2.) 175 deg C, vacuum; Yield given. Multistep reaction;

in N,N-dimethyl-formamide 1 h; Heating;

para-xylene; copper in N,N-dimethyl-formamide T=150°C; 1 h; the similar reaction without p-xylene; in presence cumene, benzoyl chloride instead p-xylene; other reagent (CuCl); other polychloroiodoarenes; tetrahalohenopyridylcopper intermediate; evidence against free radical or pyridyne intermediates; Product distributionMechanism;

para-xylene in N,N-dimethyl-formamide 23 h; Heatingthe similar reaction without p-xylene; other reaction times; similar range of products to those obtained from 4-bromotetrachloropyridine; Product distributionMechanism;