Differences in the reaction of electron deficient olefins with organocopper (I)-Lewis acid reagents and evidence for a dianionic equivalent

…, T Aoyagi, K Kitada, F Yoneda, Y Yamamoto

Index: Ibuka, Toshiro; Aoyagi, Takeshi; Kitada, Kazuko; Yoneda, Fumio; Yamamoto, Yoshinori Journal of Organometallic Chemistry, 1985 , vol. 287, p. C18 - C22

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Citation Number: 20

Abstract

Abstract Treatment of diethyl fumarate and triethoxycarbonylethylene with Bu 2 CuLi· AlCl 3 led to 1, 4-addition to give butylated products in high yields. In sharp contrast, diethyl maleate and tetraethoxycarbonylethylene predominantly gave the respective reduction products. The first evidence for a presumed dianionic intermediate by trapping with some electrophiles was also presented.