Diphenylacetylene
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.
Preparation
Preparation
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 HgO. [1]
- 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
Interesting derivatives
Interesting derivatives
- Reaction of Ph2C2 with tetraphenyl substituted cyclopentadienone results in the formation of hexaphenylbenzene.[2]
- Reaction of Ph2C2 with benzal chloride in the presence of potassium t-butoxide affords the 3-alkoxycyclopropene which coverts to the cyclopropenium ion.[3]
References
References
- ↑ Cope, A. C.; Smith, D. S.; Cotter, R. J. “Phenylacetylene” Organic Syntheses Collective Volume 4, page 377.
- ↑ Fieser, L. F. “Hexaphenylbenzene” Organic Syntheses Collective Volume 5, page 604.
- ↑ Xu, R. Breslow, R. “1,2,3-Triphenylcyclopropendium Bromide” Organic Syntheses Collective Volume 9, page 730.
See also
See also
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