30563-76-9Relevant academic research and scientific papers
Ring-chain tautomerism. Part 10 +. The reaction of oxocarboxylic acids with diazodiphenylmethane
Bowden, Keith,Misic-Vukovic, Milica M.,Ranson, Richard J.
, p. 1601 - 1606 (2007/10/03)
The rate coefficients for the esterification of a series of oxocarboxylic acids with diazodiphenylmethane have been determined in ethanol or 2-methoxyethanol at 30.0°C. These and the rates of reaction with model compounds have been used to estimate the equilibrium constants for ring-chain tautomerism for the oxocarboxylic acids.
Reactions of carbonyl compounds in basic solutions. Part 22. The mechanisms of the alkaline hydrolysis of methyl cis-3-(substituted benzoyl)-2,3-diphenylacrylates and the 5-methoxy-5-(substituted phenyl)-3,4-diphenylfuran-2(5H)-ones, as well as the ionisation of the corresponding acids
Bowden, Keith,Byrne, Jane M.
, p. 123 - 127 (2007/10/03)
Rate coefficients have been measured for the alkaline hydrolysis of a series of chain (normal) esters, the methyl cis-3-(substituted benzoyl)-2,3-diphenylacrylates, and the corresponding ring (pseudo) esters, the 5-methoxy-5-(substituted phenyl)-3,4-diphenylfuran-2(5H)-ones, in 70% (v/v) dioxane-water at 30°C. Those for the two parent esters were also measured at 45.0 and 60.0°C and the enthalpies and entropies of activation have been evaluated. A consideration of relative rates, activation parameters and substituent effects indicates hydrolysis of the chain esters with neighbouring group participation by the keto-carbonyl group. The ring esters demonstrate the high reactivity of the five-membered lactone-like system. The steric effects of the phenyl groups does not switch mechanisms, but only modifies reactivity. The equilibrium constants for ring-chain tautomerism in a series of cis-3-(substituted benzoyl)-2,3-diphenylacrylic acids have been determined by using the observed pKa values in 80% (m/m) 2-methoxyethanol-water together with estimated true pKa (pKTa) values. The equilibrium constants for these acids have been correlated using the Hammett equation to give ρ as ca. 1.3. The results are discussed in terms of steric 'bulk' and resonance effects.
Cycloaddition of Diphenylcyclopropenone with Carboximidate, Carboximidamide, and Carboximidothioate
Yoshida, Hiroshi,Sogame, Shingo,Bando, Shoichi,Nakajima, Shosuke,Ogata, Tsuyoshi,Matsumoto, Kiyoshi
, p. 3849 - 3850 (2007/10/02)
The reaction of diphenylcyclopropenone with R1N=C(R2)X (2) (R1, R2=alkyl, aryl, X=MeO, EtO, MeS, or Me2N) gave 2-pyrrolin-4-one (3) in good yield.The less reactive carboximidothioate (2, R1=4-MeC6H4, R2=Ph, X=MeS) yielded isomeric 3-pyrrolin-2-one together with 3.
