13715-59-8

Upstream product

• 1330068-60-4 C₂₃H₁₇N₃O₂ 
• 1330068-44-4 C₃₄H₂₃N₃O₂ 
• 781-43-1 9,10-dimethylanthracene 
• 1330068-62-6 C₂₂H₁₃Cl₂N₃O₂ 
• 1330068-46-6 C₂₈H₂₇N₃O₂ 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 120-12-7 anthracene 
• 10316-56-0 9,10-(4’-phenyl)urazolo-9,10-dihydroanthracene 
• 1499-10-1 9,10-diphenylanthracene 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 1450893-72-7 C₂₈H₁₉N₃O₂ 
• 1450893-71-6 C₂₂H₁₄ClN₃O₂ 

Downstream Products

• 10316-56-0 9,10-(4’-phenyl)urazolo-9,10-dihydroanthracene 
• 1330068-44-4 C₃₄H₂₃N₃O₂ 
• 1330068-60-4 C₂₃H₁₇N₃O₂ 
• 1330068-62-6 C₂₂H₁₃Cl₂N₃O₂ 
• 1330068-65-9 C₂₆H₂₃N₃O₄ 
• 13715-61-2 9,10-diethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 4233-33-4 4-Phenyl-1,2,4-triazolidine-3,5-dione 
• 781-43-1 9,10-dimethylanthracene 
• 1499-10-1 9,10-diphenylanthracene 
• 1450893-72-7 C₂₈H₁₉N₃O₂ 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 

Relevant academic research and scientific papers

Features of the Diels-Alder reaction between 9,10-diphenylanthracene and 4-phenyl-1,2,4-triazoline-3,5-dione

The Diels-Alder reaction between substituted anthracenes 1a-1j and 4-phenyl-1,2,4-triazoline-3,5 (2) is studied. In all cases except one, the reaction proceeds on the most active 9,10-atoms of substituted anthracenes. The orthogonality of the two phenyl groups at the 9,10-position of diene 1a is found to shield 9,10-reactive centers. No dienophiles with C=C bonds are shown to participate in the Diels-Alder reaction with 1a; however, the reaction 1a + 2 proceeds with the very active dienophile 2,4-phenyl-1,2,4-triazoline-3,5-dione. It is shown that attachment occurs on the less active but sterically accessible 1,4-reactive center of diene 1a. The structure of adduct 3a is proved by 1H and 13C NMR spectroscopy and X-ray diffraction analysis. The following parameters are obtained for reaction 1a + 2 ? 3a in toluene at 25°C: Keq = 2120 M-1, ΔHf≠ = 58.6 kJ/mol, ΔSf≠ = -97 J/(mol K), ΔVf≠ = -17.2 cm3/mol, ΔHb ≠ = 108.8 kJ/mol, ΔSb≠ = 7.3 J/(mol K), ΔVb≠ = -0.8 cm3/mol, ΔHr-n = -50.2 kJ/mol, ΔSr-n = -104.3 J/(mol K), ΔVr-n = -15.6 cm3/mol. It is concluded that the values of equilibrium constants of the reactions 1a-1j + 2 ? 3a-3j vary within 4 × 101-1011 M-1.

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

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

Dynamic Covalent chemistry: A facile room-temperature, reversible, diels-alder reaction between anthracene derivatives and n-phenyltriazolinedione

A series of readily accessible, dynamic Diels-Alder reactions that are reversible at room temperature have been developed between anthracene derivatives as dienes and N-phenyl-1,2,4-triazoline-3,5-dione as the dienophile. The adducts formed undergo reversible component exchange to form dynamic libraries of equilibrating cycloadducts. Furthermore, reversible adduct formation allows temperature-dependent modulation of the fluorescent properties of anthracene components; a feature of potential interest for the design of optodynamic polymeric materials by careful selection and manipulation of these simple dienes and dienophiles. Copyright