Vinyllithium
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Through Reagent
Preparation and structure
Solutions of vinyllithium are prepared by lithium-halogen exchange reactions. A halide-free route entails reaction of tetravinyltin with butyllithium:
- Sn(CH=CH2)4 + 4 BuLi → SnBu4 + 4 LiCH=CH2
The reaction of ethylene and lithium affords vinyl lithium and lithium hydride, together with other organolithium compounds,
Like most organolithium compounds, vinyllithium crystallizes from THF as a cluster compound as a cubane-type cluster.
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Reactions
Vinyllithium is used to install vinyl groups on metal-based reagents, i.e., vinylations. It is a precursor to vinylsilanes, vinylcuprates, and vinylstannanes. It adds to ketones compounds to give allylic alcohols. Vinylmagnesium bromide is often used in place of vinyllithium.
Alternative reagents
Vinyl magnesium bromide, a Grignard reagent, is in many ways easier to generate in the laboratory and behaves similarly to vinyllithium.