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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 organometallic chemistry.
Additional recommended knowledge
Several preparations for this compound exist:
- one being from benzil which is condensed with hydrazine to give the bis(hydrazone) that in turn suffers oxidation with mercury oxide.
- The compound is usually prepared from stilbene by bromination dehydrohalogenation sequence, but the product can be contaminated with stilbene, which is difficult to remove.
- One methods starts from iodobenzene and the copper salt of phenylacetylene in the Castro-Stephens coupling
- Reaction of Ph2C2 with tetraphenyl substituted cyclopentadienone results in the formation of hexaphenylbenzene.
- Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.
- ^ Cope, A. C.; Smith, D. S.; Cotter, R. J.. "Phenylacetylene". Org. Synth.; Coll. Vol. 4: 377.
- ^ Fieser, L. F.. "Hexaphenylbenzene". Org. Synth.; Coll. Vol. 5: 604.
- ^ Xu, R. Breslow, R.. "1,2,3-Triphenylcyclopropendium Bromide". Org. Synth.; Coll. Vol. 9: 730.
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Diphenylacetylene". A list of authors is available in Wikipedia.
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