1904-22-9

Usage

InChI:InChI=1/C6H7NO/c1-2-5-8-6-3-4-7/h1H,3,5-6H2

Upstream product

• 107-19-7 propargyl alcohol 
• 107-13-1 acrylonitrile 

Downstream Products

• 62172-13-8 3-[(E)-3-(Methyl-phenyl-silanyl)-allyloxy]-propionitrile 
• 62172-19-4 C₁₄H₁₉NOSi 
• 62172-14-9 C₁₄H₁₉NOSi 
• 62172-21-8 C₁₈H₁₉NOSi 
• 62172-15-0 C₁₅H₂₁NOSi 
• 62172-16-1 C₁₆H₂₃NOSi 
• 6328-48-9 3-benzyloxypropionitrile 
• 65210-60-8 7,8-dihydro-5H-pyrano[4,3-b]pyridine 
• 71-43-2 benzene 
• 1424069-93-1 3-[(1-benzyl-1,2,3-triazol-4-yl)methoxy]propanenitrile 
• 1424069-99-7 5-{2-[(1-benzyl-1H-1,2,3-triazol-4-yl)methoxy]ethyl}-1H-tetrazole 

Relevant academic research and scientific papers

Electron-rich triarylphosphines as nucleophilic catalysts for oxa-Michael reactions

Electron-rich triarylphosphines, namely 4-(methoxyphenyl)diphenylphosphine (MMTPP) and tris(4-trimethoxyphenyl)phosphine (TMTPP), outperform commonly used triphenylphosphine (TPP) in catalyzing oxa-Michael additions. A matrix consisting of three differently strong Michael acceptors and four alcohols of varying acidity was used to assess the activity of the three catalysts. All test reactions were performed with 1 mol % catalyst loading, under solvent-free conditions and at room temperature. The results reveal a decisive superiority of TMTPP for converting poor and intermediate Michael acceptors such as acrylamide and acrylonitrile and for converting less acidic alcohols like isopropanol. With stronger Michael acceptors and more acidic alcohols, the impact of the more electron-rich catalysts is less pronounced. The experimental activity trend was rationalized by calculating the Michael acceptor affinities of all phosphine-Michael acceptor combinations. Besides this parameter, the acidity of the alcohol has a strong impact on the reaction speed. The oxidation stability of the phosphines was also evaluated and the most electron-rich TMTPP was found to be only slightly more sensitive to oxidation than TPP. Finally, the catalysts were employed in the oxa- Michael polymerization of 2-hydroxyethyl acrylate. With TMTPP polymers characterized by number average molar masses of about 1200 g/mol at room temperature are accessible. Polymerizations carried out at 80°C resulted in macromolecules containing a considerable share of Rauhut-Currier-type repeat units and consequently lower molar masses were obtained.

Synthesis of polynuclear azoles linked by ether tethers

Alkylation of NH-triazoles and tetrazoles and cycloaddition of organic and inorganic azides to propargyl ethers bearing a cyano group gave a number of polynuclear heterocyclic systems bridged by ether tethers.