2395-97-3

Usage

InChI:InChI=1/C16H14O2/c1-17-15-11-7-3-5-9-13(11)16(18-2)14-10-6-4-8-12(14)15/h3-10H,1-2H3

Upstream product

• 113160-89-7 C₂₁H₂₂O₄ 
• 67-56-1 methanol 
• 120-12-7 anthracene 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 40628-55-5 9,10-dimethoxy-9,10-dihydro-9,10-epidioxidoanthracene 

Downstream Products

• 84-65-1 9,10-phenanthrenequinone 
• 30122-23-7 C₁₉H₁₈O₂ 
• 96555-78-1 11,12-dibenzoyl-9,10-dihydro-9,10-dimethoxy-9,10-ethenoanthracene 
• 189502-14-5 10-Methoxy-[9]anthrol 
• 117-80-6 2,3-Dichloro-1,4-naphthoquinone 
• 1010-60-2 2-chloro-1,4-naphthoquinone 
• 68818-86-0 9,10-Diethoxyanthracene 
• 13715-60-1 9,10-dimethoxy-14-phenyl-9,10-dihydro-9,10-[1,2]epi[1,2,4]triazolo-anthracene-13,15-dione 
• 153507-77-8 (n-Bu₃P)2Ni⁽⁰⁾(9,10-dimethoxyanthracene) 

Relevant academic research and scientific papers

Intermediates in the cleavage of endoperoxides

The decomposition of anthracene endoperoxides has been investigated under various conditions. Thermolyses proceed via radical intermediates and afford anthracenes and rearrangement products, depending on the substitution pattern. Interestingly, not only the O–O but also the C–O bond can be cleaved homolytically. Under basic conditions fragmentations take place, affording anthraquinone, and reactive oxygen species. This mechanism explains the often observed decomposition of endoperoxides during work-up. Finally, an acid-catalyzed cleavage has been observed under release of hydrogen peroxide. The results should be interesting for the mechanistic understanding of peroxide decomposition and the endoperoxides might serve as mild sources of reactive oxygen species for future applications. Copyright

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.

Electrophilic aromatic addition reaction (AdEAr) to anthracene

After finding in a previous study that naphthalene and quinoline can react via electrophilic aromatic addition reaction (AdEAr), we applied this to anthracene. When anthracene was reacted with bromine in methanol in the presence of NaHCO3 and pyridine, 9,10-dihydro-9,10-dimethoxyanthracene (2) was obtained in 82% yield in the absence of substitution products or oxidative demethylation products like anthraquinone. The same reaction in ethanol produced 9,10-diethoxy-9,10-dihydroanthracene (9) in much lower yield (45%). In addition, we investigated the reactivity of addition product 2. Treatment of 2 with DDQ in benzene at 65 °C for 12 h produced 9,10-dimethoxyanthracene (3) in 62% yield, and 2 was rapidly transformed to 9-methoxyanthracene (4) in methanolic NaOH in 10 min. Moreover, the acid-catalyzed aromatization of 2 in 1-propanol at 75 °C for 10 min gave 9-n-propoxyanthracene (8) in 65% yield.