Health Dictionary
Reliable, easy-to-read patient information on common medical conditions — written in plain language, free of jargon, and grounded in current evidence. Browse the most frequent diagnoses, understand what they mean for everyday life, and learn which steps and questions help you have a focused conversation with your doctor.
Diphenylacetylene
Introduction
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.