cas 610-48-0, 1-METHYLANTHRACENE | Articles data

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Cascade reaction for the synthesis of polycyclic aromatic hydrocarbons via transient directing group strategy
A Pd(II)-catalyzed cascade synthesis of diverse polycyclic aromatic hydrocarbons via transient directing group strategy has been developed, involving the consecutive arylation, cyclization and aromatization. The efficiency and practicality were demonstrated by wide substrate range, concise synthetic pathway and mild reaction conditions. The subsequent transformations of the benz[a]anthracene core accessed natural bioactive PAH molecules.
Wang, Ziqi,Dong, Wendan,Sun, Bing,Yu, Qinqin,Zhang, Fang-Lin
supporting information
p. 4031 - 4041
(2019/07/03)

Direct synthesis of anthracenes from o-tolualdehydes and aryl iodides through Pd(II)-Catalyzed sp3 C–H arylation and electrophilic aromatic cyclization
The first direct synthesis of substituted anthracenes from o-tolualdehydes and aryl iodides via a Pd(II)-catalyzed C–H arylation using an alcohol-bearing transient directing group and subsequent AgOTf-assisted electrophilic aromatic cyclization is described. New transient directing groups consisting of amino acids and amino alcohols enhanced the reactivity, and the C–H arylation was complete in 12 h at 90 °C. By simply changing the silver salt to silver triflate, the one-pot synthesis of anthracene derivatives was carried out using the present reaction conditions.
Park, Hyojin,Yoo, Kwangho,Jung, Byunghyuck,Kim, Min
p. 2048 - 2055
(2018/03/13)

Facile Synthesis of Polycyclic Aromatic Hydrocarbons: Br?nsted Acid Catalyzed Dehydrative Cycloaromatization of Carbonyl Compounds in 1,1,1,3,3,3-Hexafluoropropan-2-ol
The cycloaromatization of aromatic aldehydes and ketones was readily achieved by using a Br?nsted acid catalyst in 1,1,1,3,3,3-hexafluoropropan-2-ol (HFIP). In the presence of a catalytic amount of trifluoromethanesulfonic acid, biaryl-2-ylacetaldehydes and 2-benzylbenzaldehydes underwent sequential intramolecular cationic cyclization and dehydration to afford phenacenes and acenes, respectively. Furthermore, biaryl-2-ylacetaldehydes bearing a cyclopentene moiety at the α-position underwent unprecedented cycloaromatization including ring expansion to afford triphenylenes. HFIP effectively promoted the cyclizations by suppressing side reactions presumably as a result of stabilization of the cationic intermediates.
Fujita, Takeshi,Takahashi, Ikko,Hayashi, Masaki,Wang, Jingchen,Fuchibe, Kohei,Ichikawa, Junji
p. 262 - 265
(2017/01/24)

Indium-catalyzed construction of polycyclic aromatic hydrocarbon skeletons via dehydration
Polycyclic aromatic compounds can be synthesized from 2-benzylic- or 2-allylbenzaldehydes using a catalytic amount of In(III) or Re(I) complexes. By using this method, polycyclic aza-aromatic compounds can also be prepared efficiently. In these reactions, only water is formed as a side product.
Kuninobu, Yoichiro,Tatsuzaki, Tomohiro,Matsuki, Takashi,Takai, Kazuhiko
experimental part
p. 7005 - 7009
(2011/10/09)

Emission factors and importance of PCDD/Fs, PCBs, PCNs, PAHs and PM 10 from the domestic burning of coal and wood in the U.K.
This paper presents emission factors (EFs) derived for a range of persistent organic pollutants (POPs) when coal and wood were subject to controlled burning experiments, designed to simulate domestic burning for space heating. A wide range of POPs were emitted, with emissions from coal being higher than those from wood. Highest EFs were obtained for particulate matter, PM10, (～ 10 g/kg fuel) and polycyclic aromatic hydrocarbons (～ 100 mg/ kg fuel for ΣPAHs). For chlorinated compounds, EFs were highest for polychlorinated biphenyls (PCBs), with polychlorinated naphthalenes (PCNs), dibenzo-p-dioxins (PCDDs) and dibenzofurans (PCDFs) being less abundant. EFs were on the order of 1000 ng/kg fuel for ΣPCBs, 100s ng/ kg fuel for ΣPCNs and 100 ng/kg fuel for ΣPCDD/Fs. The study confirmed that mono- to trichlorinated dibenzofurans, Cl1,2,3DFs, were strong indicators of low temperature combustion processes, such as the domestic burning of coal and wood. It is concluded that numerous PCB and PCN congeners are routinely formed during the combustion of solid fuels. However, their combined emissions from the domestic burning of coal and wood would contribute only a few percent to annual U.K. emission estimates. Emissions of PAHs and PM 10 were major contributors to U.K. national emission inventories. Major emissions were found from the domestic burning for Cl1,2,3DFs, while the contribution of PCDD/F-ΣTEQ to total U.K. emissions was minor.
Lee, Robert G. M.,Coleman, Peter,Jones, Joanne L.,Jones, Kevin C.,Lohmann, Rainer
p. 1436 - 1447
(2007/10/03)

Process for producing organic compounds by catalysis of imide compounds
A process produces an organic compound by catalysis of an imide compound of Formula (1): wherein R1 and R2 are each an alkyl group, aryl group, cycloalkyl group, etc., where R1 and R2 may be combined to form a double bond, or an aromatic or non-aromatic ring; and X is an oxygen atom or a hydroxyl group. In this process, the imide compound catalyst is added in installments to the reaction system to perform a reaction. Such reactions include, for example, oxidation reactions, carboxylation reactions, nitration reactions, sulfonation reactions, and carbon-carbon bond formation reactions. This process can produce a target compound with a higher conversion or selectivity in the production of the organic compound by catalysis of the imide compound catalyst such as N-hydroxyphthalimide.
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(2008/06/13)

Characterization of the combustion products of polyethylene
Polyethylene (PE) was burned in a tube-type furnace with an air flow at a temperature of 600~900°C. Combustion products were collected with glass wool, glass fiber filter, and XAD-2 adsorbent. The analysis of the products was performed with GC-FID and GC-MSD. At low temperature, hydrocarbons were the major components, while at higher temperature the products were composed of polycyclic aromatic hydrocarbons. With the high performance of the Hewlett-Packard 6890GC-5973MSD, more compounds were identified in comparison with previous studies.
Piao, Mingjun,Chu, Shaogang,Zheng, Minghui,Xu, Xiaobai
p. 1497 - 1512
(2007/10/03)

Studies in catalytic dehydrogenation: Part X1 - Syntheses of alkylsubstituted spirol[4,6]undecanes and dehydrogenation of 1 -ethyl-8,9- benzospiro[4,6]undecane
Acylation of benzene with 2-alkylsubstituted cyclopentan-l,l-diacetic anhydrides gives the keto acids (2, R = Me, Et, Prn, Pri) which are converted into the desired alkylsubstituted spiro[4,6]undecanes 5 by Paar hydrogenation followed by cyclisation and Wolff-Kishner reduction. Catalytic dehydrogenation of l-ethyl-8,9-benzospiro[4,6]undecane 5b with Pd-C gives a complex mixture of products from which a few major products like naphthalene, 2-methylnaphthalene, l-ethylnaphthalene, 1,2-dimethylnaphthalene, 1,4,6-trimethylnaphthalene, anthracene and l-methylanthracene are identified by comparative GC-mass spectra. A plausible explanation of the formation of these products is suggested.
Lahiri, Sikha,Pal, Panchanan,Chatterjee, Gautam,Maity, Basudev,Sen
p. 768 - 773
(2007/10/03)

Chemical examination of a sea cucumber Holothuria spinifera (Holothurideae)
The ethyl acetate extract of the sea cucumber Holothuria spinifera furnishes a new steroidal glycoside, 24-methylcholesta-7,22(E)-diene-3β-O-xylopyranoside (2) along with 1-methyl-9,10-anthracenedione (1).
Anjaneyulu, A. S. R.,Raju, K. V. S.,Mallavadhani, U. V.,Prakash, C. V. S.
p. 457 - 459
(2007/10/02)

A Rapid, Convergent, and Regioselective Synthesis of Anthracenes
Anthracenes are obtained in moderate to good yield by the simultaneous treatment of benzocyclobutenols and halobenzenes with LTMP in tetrahydropyran.In the key step of this one-pot process, o-toluoyl anion intermediates from the known ring-opening of benzocyclobutenoxides add to halobenzene derived arynes.Methoxy-substituted benzocyclobutenols which are readily made regiospecifically by known methods also react regiospecifically with the single benzyne generated from either a 2- or 3-haloanisole.For example, the only trimethoxyanthracene isolated (48percent yield) from the reaction of 6-methoxybenzocyclobutenol (8) with 5-chloro-1,3-dimethoxybenzene is the 1,3,8-isomer 20.When 1,2-dihydrocyclobutaphenanthren-1-ol (14) and/or halonaphthalenes are the reactants, benzannulated anthracenes are formed; e.g., tribenzanthracene in 68percent yield from 14 and bromonaphthalene.In another extension, pentaphene (31) was made in one pot from o-dichlorobenzene.
Fitzgerald, John J.,Drysdale, Neville E.,Olofson, R. A.
p. 7122 - 7126
(2007/10/02)

Naphthocycloheptatrienylidene - a Carbene of the Tropylidene Series with Novel Properties
Naphthotropylidene (3) possesses a annulene skeleton.It can be generated by flash solvolysis of the sodium salt of naphthotropone tosylhydrazone (4') in the gas-phase.Thus 1- and 2-methylanthracene (11 and 12) are formed.The decisive step is a carb
Hackenberger, Alfred,Duerr, Heinz
p. 2644 - 2659
(2007/10/02)

Flash Vacuum Pyrolysis of 2-Methylbenzophenones and 2-Methyldiphenyl Ketimines
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Gu, Taiyin Yang,Weber, William P.
p. 2541 - 2544
(2007/10/02)

Thermal Extrusion of a One-Carbon Species from 1,2-Benzotropilidene (5H-benzocycloheptene), the Benzotropyl (Benzocycloheptenyl) Free Radical, 1,2:5,6-Dibenzotropilidene (5H-Dibenzocycloheptene), and the 1,2:4,5-Dibenzotropyl (Dibenzocycloheptenyl) Free Radical
The benzotropyl dimer 7,7'-bis(3,4-benzotropyl) (6) has been prepared and thermolyzed (400 deg C) both without and with added benzene.In addition, 1,2:5,6-dibenzotropilidene (3) and 7,7'-bis(1,2:5,6-dibenzotropyl) (7) have been pyrolyzed (430 deg C) both without and with added naphthalene.The similarity of the products obtained in the former pyrolysis, namely, naphthalene (12), α-methylnaphthalene (13), β-methylnaphthalene (14), 1,2-benzocyclohepta-1,3-diene (15), benzocycloheptene (16) and toluene (whwn benzene is used), with those obtained from pyrolysis of 1,2-benzotropilidene (1) confirms that both thermolyses involve the benzotropyl radical.The similarity of the products from the latter two pyrolyses (of 3 and 7), namely, anthracene (4), 9-methylanthracene (5), 9,10-dihydroanthracene (17), 1,2:4,5-dibenzo-1,4-cycloheptadiene (20), 1- and 2-methylanthracene (18 and 19), and, when naphthalene (12) was used, benzotropilidene (1) and 1- and 2-methylnaphthalene (13 and 14), shows that both of these go through a common intermediate, the 1,2:4,5-dibenzotropyl radical (8). 9-Methylanthracene (5) was shown to thermally produce anthracene (4) and 1- and 2-methylanthracene (18 and 19), but, even with this complication, anthracene (4) was shown to be a primary product from the pyrolysis of dibenzotropilidene (3).Attempts to use di-tert-butyl nitroxide (21) as an initiator (400 deg C) gave primarily Diels-Alder addition of the isobutylene formed by decomposition of the nitroxide with both 1,2:4,5-dibenzotropilidene (the product of a 1,5-hydrogen shift in 3) and 9-methylanthracene (5).A lower temperature (345 deg C) reaction of 3 with naphthalene in the presence of nitroxide 21 did produce anthracene (4) and benzotropilidene (1) in addition to the Diels-Alder adduct, confirming the free-radical nature of the reaction.Low-temperature control experiments employing the benzotropyl dimer (6) (280 deg C) and the dibenzotropyl dimer (7) (345 deg C) showed that they were undergoing cleavage to their respective radicals (2 and 8) and that these were giving product directly, rather than the benzo- and dibenzotropilidenes (1 and 3), which were being formed in the reactions by hydrogen abstraction, giving the products.It has thus been demonstrated that the benzo- and dibenzotropyl radicals (2 and 8) can transfer a CH group to an aromatic acceptor and that the pyrolytic reactions of benzo- and dibenzotropilidenes (1 and 3) to give naphthalene and anthracene are CH-transfer reactions of the tropyl radicals formed by hydrogen abstraction.Yields of up to 65percent of anthracene (4) have been realized in the pyrolyses of dibenzotropilidene (3).Mechanisms for these CH-transfer reactions are presented.A contrast is made between the low-temperature reaction of the dibenzotropyl dimer (7) which (345 deg C) gives only anthracene and dibenzotropilidene (3), by CH loss and hydrogen abstraction, respectively, and the low-temperature (280 deg C) reaction of benzotropyl dimer (6) which not only gives naphthalene (12) and benzotropilidene (1) by CH loss and hydrogen ...
Pomerantz, Martin,Combs, Gerald L.,Fink, Rina
p. 143 - 149
(2007/10/02)

Molecular structure and estrogenic activity. Synthesis and properties of tetrahydroanthracenic isomers of acids of the doisynolic series
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Dvolaitzky,Jacques,Azadian Boulanger
p. 607 - 614
(2007/10/06)