Carbanions. XVI. Reactions of 4-chloro-1-p-biphenylylbutane with alkali metals. Formation of a spiro anion

E Grovenstein Jr, S Akabori

Index: Grovenstein,E.; Akabori,S. Journal of the American Chemical Society, 1975 , vol. 97, # 16 p. 4620 - 4626

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Citation Number: 16

Abstract

Abstract: 4-Chloro-Ip-biphenylylbutane reacts with lithium in THF at-70'to give a mixture of 4- p-biphenylylbutyllith-ium and 8-phenylspiro [4.5]-6, 8-decadienyllithium (7). With potassium, cesium, and Cs-K-Na alloy chiefly the spiro anion (7) and a little 1-p-biphenylylbutyl anion (6) are formed. Experiments with sodium and potassium, in which dioxane or tertiary alcohols were used as a proton source to" trap" intermediate anions, indicate that 4-p- ...