72612-74-9Relevant articles and documents
Effect of solvent and temperature on the lithium?bromine exchange of vinyl bromides: Reactions of n -butyllithium and t -butyllithium with (E)-5-bromo-5-decene
Bailey, William F.,Luderer, Mark R.,Uccello, Daniel P.,Bartelson, Ashley L.
, p. 2661 - 2666 (2010)
The outcome of reactions of (E)-5-bromo-5-decene (1), a representative vinyl bromide, with t-BuLi or n-BuLi at 0 °C and room temperature, respectively, in a variety of solvent systems has been investigated. Vinyl bromide 1 does not react with t-BuLi in pure heptane; however, the presence of even small quantities of an ether in a predominantly heptane medium resulted in virtually complete consumption of 1 at 0 °C, resulting in nearly the same distribution of products, including 60?80% of (Z)-5-decenyllithium, regardless of the solvent composition. Vinyl bromide 1 reacts slowly with n-BuLi at room temperature in a variety of ether and heptane-ether mixtures to afford a mixture of products including significant quantities of recovered starting material. The results of these experiments demonstrate that lithium?bromine exchange between a vinyl bromide and either t-BuLi or n-BuLi at temperatures significantly above ?78 °C is not an efficient method for the generation of a vinyllithium.
