Collect. Czech. Chem. Commun. 1980, 45, 3488-3501

Metal-oxide induced redox chain addition of tetrachloromethane to a carbon-carbon double bond

Milan Hájek, Přemysl Šilhavý and Jaroslav Málek

Institute of Chemical Process Fundamentals, Czechoslovak Academy of Sciences, 165 02 Prague 6-Suchdol


Formation of 1 : 1 adducts in the addition of tetrachloromethane to a terminal carbon-carbon double bond was investigated at 76-200 °C. The redox chain addition reaction with 1-octene, electron-deficient alkenes and unconjugated aliphatic dienes induced by catalytic amounts of copper(I) or copper(II) oxides in conjugation with diethylamine or diisopropylamine afforded the corresponding 1 : 1 adducts up to in 85% yields. Aliphatic 1,3-dienes underwent redox chain 1,4-addition giving isomeric 1,1,1,5-tetrachloro-3-alkenes.