187676-86-4

Upstream product

• 92-91-1 biphenyl-4-acetaldehyde 
• 108-86-1 bromobenzene 
• 2001-23-2 1-(biphenyl-4-yl)-2-phenylethanone 
• 98-04-4 phenyltrimethylammonium iodide 
• 591-50-4 iodobenzene 
• 37940-57-1 1-biphenyl-4-yl-propan-1-one 
• 103-80-0 phenylacetyl chloride 
• 92-52-4 biphenyl 
• 74-88-4 methyl iodide 

Downstream Products

• 180262-11-7 1-(4-biphenyl)-2-phenyldiazopropane 
• 187676-94-4 [1-Biphenyl-4-yl-2-phenyl-prop-(E)-ylidene]-hydrazine 

Relevant academic research and scientific papers

Selective α-Methylation of Aryl Ketones Using Quaternary Ammonium Salts as Solid Methylating Agents

We describe the use of phenyl trimethylammonium iodide (PhMe3NI) as an alternative methylating agent for introducing a CH3group in α-position to a carbonyl group. Compared to conventional methylating agents, quaternary ammonium salts have the advantages of being nonvolatile, noncancerogenic, and easy-to-handle solids. This regioselective method is characterized by ease of operational setup, use of anisole as green solvent, and yields up to 85%.

Transition-Metal-Free α-Arylation of Enolizable Aryl Ketones and Mechanistic Evidence for a Radical Process

The α-arylation of enolizable aryl ketones can be carried out with aryl halides under transition-metal-free conditions using KOtBu in DMF. The α-aryl ketones thus obtained can be used for step- and cost-economic syntheses of fused heterocycles and Tamoxifen. Mechanistic studies demonstrate the synergetic role of base and solvent for the initiation of the radical process.

Control of carbene reactivity by crystals. A highly selective 1,2-H shift in the solid-to-solid reaction of 1-(4'-biphenylyl)-2-phenyldiazopropane to (Z)-1-(4'-biphenylyl)-2-phenylpropene

Ruby red polycrystalline samples of 1-(4'-biphenylyl)-2-phenyldiazopropane (1a) efficiently transform into colorless (Z)-1-(4'-biphenylyl)-2-phenylpropene [(Z)-3a] in up to 96% yield in a highly selective photochemical solid-to-solid reaction. The solid state reaction was shown to proceed via a carbene intermediate, and it was formulated as a 1,2-H shift with unprecedented stereoselectivity. It was shown that irradiation of la in inert solvents gives products via 1,2-H shifts [(Z)-3a and (E)-3a] and 1,2-Ph migrations [(Z)-4a and (E)-4a] in yields that vary strongly with the polarity of solvent. Irradiation of 1a in ethanol gave similar products along with ethers 5a from insertion of the carbene into the EtO-H bond.