Collect. Czech. Chem. Commun. 1979, 44, 1608-1612

Radical addition of lactones to 1-alkenes initiated by cupric oxide

Milan Hájek, Božena Špirková and Jaroslav Málek

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


γ-Butyrolactone and γ-valerolactone react with 1-alkenes such as 1-octene and 1-decene, in the presence of cupric oxide as initiator to form the corresponding 2-n-alkyl-γ-butyrolactone and 2-n-alkyl-γ-valerolactone. Yields of these 1 : 1 adducts vary between 41 and 82% and depend on the lactone to 1-alkene molar ratio and on the procedure used for preparation of the metal oxide. The most efficient is the cupric oxide obtained by oxidation of copper powder in a stream of oxygen at 300 °C or by a similar oxidation of a CuO-Cu2O-Cu mixture resulting from cupric oxide during the radical addition reaction.