Diphenylacetylene is the

chemical compound A chemical compound is a chemical substance composed of many identical molecules (or molecular entities) containing atoms from more than one chemical element held together by chemical bonds. A molecule consisting of atoms of only one element ...

C₆H₅C≡CC₆H₅. The molecule consists of two

phenyl In organic chemistry, the phenyl group, or phenyl ring, is a cyclic group of atoms with the formula C6 H5, and is often represented by the symbol Ph. Phenyl group is closely related to benzene and can be viewed as a benzene ring, minus a hydrogen ...

groups attached to a C₂ unit. A colorless solid, it is used as a building block in organic synthesis and as a

ligand In coordination chemistry, a ligand is an ion or molecule ( functional group) that binds to a central metal atom to form a coordination complex. The bonding with the metal generally involves formal donation of one or more of the ligand's elec ...

in organometallic chemistry.

Preparation and structure

In one preparation for this compound,

benzil Benzil (i.e. Bz2, systematically known as 1,2-diphenylethane-1,2-dione) is the organic compound with the formula ( C6H5 CO)2, generally abbreviated ( PhCO)2. This yellow solid is one of the most common diketones. Its main use is as a photoinitia ...

is condensed with hydrazine to give the bis(hydrazone), which is oxidized with

mercury(II) oxide Mercury(II) oxide, also called mercuric oxide or simply mercury oxide, is the inorganic compound with the formula Hg O. It has a red or orange color. Mercury(II) oxide is a solid at room temperature and pressure. The mineral form montroydite is v ...

. Alternatively

stilbene Stilbene may refer to one of the two stereoisomers of 1,2-diphenylethene: * (''E'')-Stilbene (''trans'' isomer) * (''Z'')-Stilbene (''cis'' isomer) See also * Stilbenoid Stilbenoids are hydroxylated derivatives of stilbene. They have a C6– ...

is brominated, and the resulting dibromodiphenylethane is subjected to

dehydrohalogenation In chemistry, dehydrohalogenation is an elimination reaction which removes a hydrogen halide from a substrate. The reaction is usually associated with the synthesis of alkenes, but it has wider applications. Dehydrohalogenation from alkyl halid ...

, Yet another method starts involves the coupling

iodobenzene Iodobenzene is an organoiodine compound consisting of a benzene ring substituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry. It is a volatile colorless liquid, although aged samples appear yellowish. Pre ...

and the copper salt of phenylacetylene in the Castro-Stephens coupling. Diphenylacetylene is a planar molecule. The central C≡C distance is 119.8 picometers.

Derivatives

Reaction of diphenylacetylene with tetraphenylcyclopentadienone results in the formation of hexaphenylbenzene in a Diels–Alder reaction. Reaction of Ph₂C₂ with

benzal chloride Benzal chloride is an organic compound with the formula C6H5CHCl2. This colourless liquid is a lachrymator and is used as a building block in organic synthesis. Preparation and usage Benzal chloride is produced by the free radical chlorination o ...

in the presence of potassium ''t''-butoxide affords the 3-alkoxy

cyclopropene Cyclopropene is an organic compound with the formula . It is the simplest cycloalkene. Because the ring is highly strained, cyclopropene is difficult to prepare and highly reactive. This colorless gas has been the subject for many fundamental st ...

which converts to the

cyclopropenium ion The cyclopropenium ion is the cation with the formula . It has attracted attention as the smallest example of an aromatic cation. Its salts have been isolated, and many derivatives have been characterized by X-ray crystallography. The cation and so ...

.{{cite journal, first1 = Ruo, last1 = Xu, first2 = Ronald, year=1997, last2 = Breslow, title = 1,2,3-Triphenylcyclopropenium Bromide, journal=Organic Syntheses , volume = 74, pages = 72, doi = 10.15227/orgsyn.074.0072

References

Phenyl compounds Alkyne derivatives