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All feature three contiguous sp²-hybridized carbon centers and all derive stability from resonance. [6] Each species can be presented by two resonance structures with the charge or unpaired electron distributed at both 1,3 positions. Resonance structure of the allyl anion. The cation is identical, but carries an opposite-sign charge. [7]
β-Carbon elimination (beta-carbon elimination) is a type of reaction in organometallic chemistry wherein an allyl ligand bonded to a metal center is broken into the corresponding metal-bonded alkyl (aryl) ligand and an alkene. [1] It is a subgroup of elimination reactions.
Vinyl, aryl and tertiary alkyl halides are unreactive; as a result, the reaction of NaI in acetone can be used as a qualitative test to determine which of the aforementioned classes an unknown alkyl halide belongs to, with the exception of alkyl iodides, as they yield the same product upon substitution.
β-Hydride elimination is a reaction in which a metal-alkyl centre is converted into the corresponding metal-hydride-alkene. [1] β-Hydride elimination can also occur for many alkoxide complexes as well. The main requirements are that the alkyl group possess a C-H bond β to the metal and that the metal be coordinatively unsaturated.
Lithium–halogen exchange is frequently used to prepare vinyl-, aryl- and primary alkyllithium reagents. Vinyl halides usually undergo lithium–halogen exchange with retention of the stereochemistry of the double bond. [2] The presence of alkoxyl or related chelating groups accelerates lithium–halogen exchange. [3]
In the variation developed by Knochel et al, aryl zinc bromides were reacted with vinyl triflates and vinyl halides. [27] Reactions between sp 3-sp 3 centers are often more difficult; however, adding an unsaturated ligand with an electron withdrawing group as a cocatalyst improved the yield in some systems. It is believed that added ...
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