DIFFERENCES IN THE REACTION OF ELECTRON DEFICIENT OLEFINS WITH ORGANOCOPPER(I)-LEWIS ACID REAGENTS AND EVIDENCE FOR A DIANIONIC EQUIVALENT

Article abstract of DOI:10.1016/0022-328X(85)80081-4

Treatment of diethyl fumarate and triethoxycarbonylethylene with Bu2CuLi*AlCl3 led to 1,4-addition to give butylated products in high yields.In sharp contrast, diethyl meleate and tetraethoxycarbonylethylene predominantly gave the respective reduction products.The first evidence for a presumed dianionic intermediate by trapping with some electrophiles was also presented.