Phenyllithium

• Lithiumphenyl
• Liph

Fixed

150 ° C ( decomposition)

Reacts violently with water

Phenyllithium solution in dibutyl

Attention

Phenyllithium solution, technical, 1.8-2.1 M in cyclohexane / ether ( 7:3)

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Phenyl is an organometallic compound of the element lithium, and thus one of the organolithium compounds.

Production and representation

Phenyllithium is prepared from metallic lithium, and bromobenzene or chlorobenzene analogous to the Grignard reagent.

Another way of representing the reaction of benzene with n-butyllithium. As more CH-acidic compound to n- BuLi to benzene can be metalated as the presence of σ -donors (eg TMEDA).

TMEDA cleaves the present in solution of n-BuLi oligomer into monomers and polarizes the Li -C bond by these complexes.

Properties

Phenyllithium crystallized in the solid state in an infinite polymeric ladder structure. The binding of the ipso carbon of the two lithium atoms in the dimeric Li2C2 subunits based on a 2- electron -3 center bond (2e - 3c). In addition, there is a strong interaction of π electrons of the phenyl rings of the lithium atoms of the adjacent units.

In phenyllithium solution can form a variety of structures which depend on the solvent. Are known monomeric, dimeric, trimeric (6- membered ring ), tetrameric ( heterocubane ) and hexameric ( octahedron, hexagonal) structures.

In THF phenyllithium is a mixture of monomers and dimers, dimer and dimer in TMEDA in diethyl ether and tetramer before.

Use

Is phenyl (for example in the formation of biphenylene by nucleophilic aromatic substitution reactions ) are used in organic chemistry to a number of syntheses. It is this in technical form as small percent solution (usually about 20%) in various solvents such as dibutyl ether, cyclohexane / ether before.

Safety

Phenyllithium is corrosive, highly flammable, highly reactive and reacts violently with water.