Diphenylacetylene
Encyclopedia
Diphenylacetylene is the chemical compound
C6H5C≡CC6H5. The molecule consists of phenyl groups attached to both ends of an alkyne
. It is a colorless crystalline material that is widely used as a building block in organic
and as a ligand in organometallic chemistry
.
Chemical compound
A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...
C6H5C≡CC6H5. The molecule consists of phenyl groups attached to both ends of an alkyne
Alkyne
Alkynes are hydrocarbons that have a triple bond between two carbon atoms, with the formula CnH2n-2. Alkynes are traditionally known as acetylenes, although the name acetylene also refers specifically to C2H2, known formally as ethyne using IUPAC nomenclature...
. It is a colorless crystalline material that is widely used as a building block in organic
Organic synthesis
Organic synthesis is a special branch of chemical synthesis and is concerned with the construction of organic compounds via organic reactions. Organic molecules can often contain a higher level of complexity compared to purely inorganic compounds, so the synthesis of organic compounds has...
and as a ligand in organometallic chemistry
Organometallic chemistry
Organometallic chemistry is the study of chemical compounds containing bonds between carbon and a metal. Since many compounds without such bonds are chemically similar, an alternative may be compounds containing metal-element bonds of a largely covalent character...
.
Preparation
Several preparations for this compound exist:- benzilBenzilBenzil is the organic compound with the formula 2, generally abbreviated 2. This yellow solid is one of the most common diketones...
is condensed with hydrazineHydrazineHydrazine is an inorganic compound with the formula N2H4. It is a colourless flammable liquid with an ammonia-like odor. Hydrazine is highly toxic and dangerously unstable unless handled in solution. Approximately 260,000 tons are manufactured annually...
to give the bis(hydrazone), which is oxidized with mercury oxideMercury oxideMercury oxide can refer to:* Mercury oxide , Hg2O* Mercury oxide , HgO...
. - stilbeneStilbene-Stilbene, is a diarylethene, i.e., a hydrocarbon consisting of a trans ethene double bond substituted with a phenyl group on both carbon atoms of the double bond. The name stilbene is derived from the Greek word stilbos, which means shining....
is brominated, then dehydrohalogenatedDehydrohalogenationDehydrohalogenation is an organic reaction from which an alkene is obtained from an alkyl halide . It is also called a β-Elimination reaction and is a type of elimination reaction....
, but the product can be contaminated with stilbene, which is difficult to remove. - One method starts from iodobenzeneIodobenzeneIodobenzene is an organic compound consisting of a benzene ring substitituted with one iodine atom. It is useful as a synthetic intermediate in organic chemistry.-Preparation:...
and the copper salt of phenylacetylene in the Castro-Stephens couplingCastro-Stephens couplingThe Castro-Stephens Coupling is a cross coupling reaction between a copper acetylide and an aryl halide forming a disubstituted alkyne and a copper halide....
Interesting derivatives
- Reaction of Ph2C2 with tetraphenylcyclopentadienoneTetraphenylcyclopentadienoneTetraphenylcyclopentadienone is a dark purple to black crystalline solid at standard temperature and pressure. Because of its highly conjugated nature, this organic compound can be analyzed in the UV spectrum. Tetraphenylcyclopentadienone has a "propeller" shape in its 3D conformation...
results in the formation of hexaphenylbenzeneHexaphenylbenzeneHexaphenylbenzene is an aromatic compound composed of a benzene ring substituted with six phenyl rings.It may be prepared through a Diels-Alder reaction by refluxing tetraphenylcyclopentadienone and diphenylacetylene in benzophenone or other high-temperature solvent.-Structure:Due to steric...
. - Reaction of Ph2C2 with benzal chlorideBenzal chlorideBenzal 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....
in the presence of potassium t-butoxide affords the 3-alkoxycyclopropeneCyclopropeneCyclopropene is an organic compound with the formula 34. It is the simplest isolable cycloalkene. It has a triangular structure. Because the ring is highly strained, cyclopropene is both difficult to prepare and interesting to study. Like cyclopropane, the carbon ring of cyclopropene is planar...
which coverts to the cyclopropenium ion.