10316-56-0Relevant articles and documents
Reactivity Variation of Tetracyanoethylene and 4-Phenyl-1,2,4-Triazoline-3,5-Dione in Cycloaddition Reactions in Solutions
Kiselev, Vladimir D.,Kornilov, Dmitry A.,Anikin, Oleg V.,Shulyatiev, Alexey A.,Konovalov, Alexander I.
, p. 31 - 44 (2019)
The reasons for the very high reactivity and variability of reactivity of two dienophiles, tetracyanoethylene (1) and 4-phenyl-1,2,4-triazoline-3,5-dione (2), in the Diels–Alder reactions were considered. The data on the rate of reactions with anthracene (3), benzanthracene (4) and dibenzanthracene (5) in 14 solvents over a range of temperatures and high pressures, data on the change in the enthalpy of solvation of reagents, transition state, and adducts in the forward and backward reactions, and the enthalpies of these reactions in solution were obtained. Strong π-acceptor dienophile 1 has sharply reduced reactivity in reactions in π-donor aromatic solvents. It was observed that the π-acceptor properties of dienophile 1 disappear upon passage to the transition state and adduct. Large solvent effects on the reaction rate can be predicted for all types of reactions involving tetracyanoethylene. Very high reactivity of dienophiles 1 and, especially, 2 can be useful to catch such carcinogenic impurities such as 3–5 and neutralize them by transformation into less dangerous adducts.
Diels-Alder reaction rate in the solid state and the evidence of the location of molecular complexes between the reagents on the reaction pathway
Kiselev, Vladimir D.,Kolesnikova, Anastasia O.,Dinikaev, Ildar F.,Shulyatiev, Alexey A.,Klimovitskii, Alexander E.,Kornilov, Dmitry A.
, p. 207 - 212 (2020/10/02)
The rate of reactions in the solid phase with uniform grinding of crystals of dienes, anthracene, and 9,10-dimethylanthracene, with dienophiles, tetracyanoethylene, N-phenylmaleimide, and 4-phenyl-1,2,4-triazoline-3,5-dione, has been studied. It was shown
Homo-Diels-Alder reaction of a very inactive diene, bicyclo[2,2,1]hepta-2, 5-diene, with the most active dienophile, 4-phenyl-1,2,4-triazolin-3,5-dione. Solvent, temperature, and high pressure influence on the reaction rate
Kiselev, Vladimir D.,Shakirova, Ilzida I.,Kornilov, Dmitry A.,Kashaeva, Helen A.,Potapova, Lubov N.,Konovalov, Alexander I.
, p. 47 - 53 (2013/03/13)
Solvent, temperature, and high pressure influence on the rate constant of homo-Diels-Alder cycloaddition reactions of the very active hetero-dienophile, 4-phenyl-1,2,4-triazolin-3,5-dione (1), with the very inactive unconjugated diene, bicyclo[2,2,1]hepta