22872-40-8

Upstream product

• 75-36-5 acetyl chloride 
• 164594-13-2 Phenyl[2-(trimethylsilyl)phenyl]iodonium trifluoromethanesulfonate 
• 107-12-0 propiononitrile 
• 52923-47-4 (Z)-1-Cyano-1-phenyl-propen-2-ol anion 
• 74-88-4 methyl iodide 
• 77-78-1 dimethyl sulfate 
• 4468-48-8 1-phenyl-1-cyanopropan-2-one 
• 80-48-8 methyl p-toluene sulfonate 

Downstream Products

• 104367-49-9 2-methyl-2-phenylpent-4-enenitrile 

Relevant academic research and scientific papers

Facile one-pot synthesis of 2-aryl-substituted nitriles and 2-aryl-3-keto nitriles via benzyne reaction

2-Aryl-substituted nitriles were prepared in good to excellent yields in a one-pot reaction by the reaction of benzyne, generated using neutral conditions from (phenyl)[o-(trimethylsilyl)-phenyl]iodonium triflate, and 2-lithionitriles. 3-Keto nitriles substituted at the 2-position were obtained in good yields when these reactions were trapped with acid chlorides. The mechanism of the benzyne reaction in terms of a N-lithiobenzocyclobutanimine intermediate is discussed. Copyright Taylor & Francis Group, LLC.

MESOMERIC ANIONS. X. METHYLATION OF ALKALI-METAL DERIVATIVES OF SOME 1,3-KETONITRILES

The effect of polar factors on the relative nucleophilicity of the oxygen and carbon reaction centers in the alkali-metal derivatives of 2-(X-benzoyl)acetonitriles, 2-(X-benzoyl)propionitriles, and 2-(X-phenyl)acetylacetonitriles was investigated.During methylation with methyl iodide and methyl p-toluenesulfonate in DMFA the ratio of the C- and O-methylation products for all the investigated compounds decreases with increase in the accepting power of the substituent X.It was shown that the sensitivity of the C-reaction center to the effect of the substituent X is greater than that of the O-center.

The Allopolarization Principle and its Applications, IV. Substituent Effects in the Methylation of Enolate Anions

The ratio of O- and C-methylated products in the reaction of the sodium salts of acetophenones 1, propiophenones 3, phenylacetones 5, β-dicarbonyl compounds 12, α-cyanocarbonyl compounds 13, acetaldehyde, propionaldehyde, and diethylketone with dimethyl sulfate, methyl iodide, and trimethyl phosphate in HMPTA has been determined with regard to the effect of substituents.In some cases the influence of solvents, concentration and temperature has also been studied.