Diphenylzinc

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Diphenylzinc
Skeletal formula of diphenylzinc monomer
Ball-and-stick model of the diphenylzinc monomer molecule
Identifiers
1078-58-6 YesY
Jmol 3D model Interactive image
Properties
C12H10Zn
Molar mass 219.59 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Diphenylzinc is an organozinc compound. It is commonly used as the synthetic equivalent of a Ph synthon. Solvent-free diphenylzinc exists as dimeric PhZn(μ-Ph)2ZnPh molecules in solid state.[1]

Skeletal formula of diphenylzinc dimer
Ball-and-stick model of the diphenylzinc dimer molecule
The dimeric solid state form of diphenylzinc.

Diphenylzinc is commercially available. It may be prepared by reaction of phenyllithium with zinc bromide:[2]

2 PhLi + ZnBr2 → Ph2Zn + 2 LiBr

It may also be prepared by the reaction of diphenylmercury with zinc metal.[3]

References[edit]

  1. ^ Markies, Peter R.; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, Friedrich; Smeets, Wilberth J. J.; Spek, Anthony L. (1990). "Coordinational behavior of solvent-free diorganylzinc compounds: the remarkable x-ray structure of dimeric diphenylzinc". Organometallics. 9 (8): 2243. doi:10.1021/om00158a022. 
  2. ^ Curtin, David Y.; Tveten, John L. (1961). "Reaction of Diarylzinc Reagents with Aryldiazonium Salts. Direct Formation of cis-Azo Compounds". J. Org. Chem. 26 (6): 1764. doi:10.1021/jo01065a017. 
  3. ^ Markies, P; Schat, Gerrit; Akkerman, Otto S.; Bickelhaupt, F.; Spek, Anthony L. (1992). "Complexation of diphenylzinc with simple ethers. Crystal structures of the complexes Ph2Zn·glyme and Ph2Zn·diglyme". J. Organomet. Chem. 430: 1. doi:10.1016/0022-328X(92)80090-K.