Vinyllithium

A colorless or white solid, it is encountered mainly as a solution in tetrahydrofuran (THF).

[1] Solutions of vinyllithium are prepared by lithium-halogen exchange reactions.

A halide-free route entails reaction of tetravinyltin with butyllithium: The reaction of ethylene and lithium affords vinyl lithium and lithium hydride, together with other organolithium compounds,[1] Like most organolithium compounds, vinyllithium crystallizes from THF as a cluster compound as a cubane-type cluster.

[3] It adds to ketones compounds to give allylic alcohols.

[4] Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.

Structure of [LiC 2 H 3 (THF)] 4 .