Diphenylzinc is an
organozinc compound
Organozinc compounds in organic chemistry contain carbon (C) to zinc (Zn) chemical bonds. Organozinc chemistry is the science of organozinc compounds describing their physical properties, synthesis and reactions.The Chemistry of Organozinc Compoun ...
. It is commonly used as the synthetic equivalent of a Ph
− synthon
In retrosynthetic analysis, a synthon is a hypothetical unit within a target molecule that represents a potential starting reagent in the retroactive synthesis of that target molecule. The term was coined in 1967 by E. J. Corey. He noted in 1 ...
. Solvent-free diphenylzinc exists as dimeric molecules in the solid state.
Diphenylzinc is commercially available. It may be prepared by reaction of
phenyllithium
Phenyllithium or lithobenzene is an organometallic agent with the empirical formula C6H5Li. It is most commonly used as a metalating agent in organic syntheses and a substitute for Grignard reagents for introducing phenyl groups in organic synthes ...
with
zinc bromide
Zinc bromide ( Zn Br2) is an inorganic compound with the chemical formula Zn Br2. It is a colourless salt that shares many properties with zinc chloride (ZnCl2), namely a high solubility in water forming acidic solutions, and good solubility in o ...
:
:2 PhLi + ZnBr
2 → Ph
2Zn + 2 LiBr
It may also be prepared by the reaction of
phenylmagnesium bromide with
zinc chloride
Zinc chloride is the name of inorganic chemical compounds with the formula ZnCl2 and its hydrates. Zinc chlorides, of which nine crystalline forms are known, are colorless or white, and are highly soluble in water. This salt is hygroscopic and e ...
or
diphenylmercury
Diphenylmercury is the organomercury compound with the formula Hg(C6H5)2. It is a white solid. The compound is of historic interest as a particularly stable organometallic compound but it finds few uses because of its high toxicity.
Preparation
...
with zinc metal.
References
{{Zinc compounds
Organozinc compounds
Phenyl compounds