781-92-0Relevant academic research and scientific papers
Hyperconjugative and Inductive Perturbations in Poly(p-phenylene vinylenes)
Kim, Youngmi,Zhu, Zhengguo,Swager, Timothy M.
, p. 452 - 453 (2004)
New polymers having high solid-state fluorescence quantum yields and the ability to tune their electron affinity without effecting their band gap using hyperconjugative interactions is reported. The novel three-dimensional poly(phenylene vinylenes) having [2.2.2] bicyclic ring systems shown were synthesized, and the different hyperconjugative perturbations provide differential fluorescence sensory quenching responses to electron-rich and electron-deficient analytes in solution and solid thin films. Copyright
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
Fujita, Takeshi,Takahashi, Ikko,Hayashi, Masaki,Wang, Jingchen,Fuchibe, Kohei,Ichikawa, Junji
, p. 262 - 265 (2017/01/24)
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.
BF3-H2O catalyzed hydroxyalkylation of aromatics with aromatic aldehydes and dicarboxaldehydes: Efficient synthesis of triarylmethanes, diarylmethylbenzaldehydes, and anthracene derivatives
Prakash, G. K. Surya,Panja, Chiradeep,Shakhmin, Anton,Shah, Eric,Mathew, Thomas,Olah, George A.
supporting information; experimental part, p. 8659 - 8668 (2009/12/30)
(Figure Presented) BF3-monohydrate is found to be an efficient and strong acid catalyst as well as an effective protosolvating medium suitable for the hydroxyalkylation of arenes with aromatic aldehydes. This reaction has been extended to aromatic dialdehydes, such as terephthalic dicarboxaldehyde and isoterephthalic dicarboxaldehyde, for the efficient synthesis of diarylmethylbenzaldehydes, which are useful synthons for various organic transformations. Further, successful one step convergent synthesis of various synthetically useful anthracene derivatives from phthalaldehyde was also achieved. BF3-H2O is less expensive and acts as an efficient substitute for nonoxidizing strong protic acids/superacids.
A new InCl3-catalyzed reduction of anthrones and anthraquinones by using aluminum powder in aqueous media
Wang, Chunyan,Wan, Jieping,Zheng, Zhiguo,Pan, Yuanjiang
, p. 5071 - 5075 (2008/02/01)
InCl3-catalyzed reduction of anthrones and anthraquinones was investigated under different conditions. A new synthetic method for anthracenes in aqueous media under mild conditions is described.
Chemical syntheses of syn- and anti-1,2;3,4-diepoxides derived from 1,4-dimethyl-and 1,2,3,4-tetramethylanthracenes and naphthalenes
Rigaudy, Jean,Lachgar, Mohamed,Caspar, Alain,Chassagnard, Claude
, p. 481 - 490 (2007/10/03)
Chemical isomerization of 1,4-endoperoxides 1a,b,n derived from meso-unsubstituted 1,4-dimethyl- or 1,2,3,4-tetramethylanthracenes (and naphthalenes) to syn-1,2;3,4-diepoxides 2a,b,n has been achieved by treatment at room temperature with FeSO4 in CH3CN containing pyridine. With analogous 9,10-diphenyl derivatives 1c,d, heating appears necessary and the same isomerization is then superseded by another type of rearrangement leading to dihydronaphthoxanthenols 4c,d. An electron-exchange mechanism may explain the difference between both series. In contrast, the isomeric anti-1,2;3,4-diepoxides 19b,c,d,n have been prepared by direct epoxidation of the hydrocarbons 18a-d,n with dimethyldioxirane generated in situ. In this case, the reaction is more efficient for 9,10-diphenyl derivatives 18c,d than for meso-unsubstituted ones 18a,b as the latter can undergo competitive oxidations at meso-positions leading to 10-hydroxy-9-anthrones 22a,b at the same time as anthraquinones 23a,b. Elsevier.
An Efficient Reduction of Anthrones to Anthracenes
Marquardt, Donald J.,McCormick, Frankie A.
, p. 1131 - 1134 (2007/10/02)
An efficient and general means of reducing anthrones to anthracenes has been developed.The procedure, which uses NaBH4 as the reducing agent in a mixed solvent system of diglyme/methanol, produced anthracenes in essentially quantitative yield from a variety of anthrones.
Transformations photochimiques d'endoperoxydes derives d'hydrocarbures aromatiques polycycliques III. Photo-isomerisation d'endoperoxydes-1,4 tetrahydroaromatiques
Rigaudy, Jean,Baranne-Lafont, Joele,Ranjon, Andre,Caspar, Alain
, p. 187 - 194 (2007/10/02)
In a previous papers, the thermal and photochemical isomerization of anthracenic 9,10-endoperoxides into unstable meso-diepoxides has been reported.We have now investigated the behaviour of tetrahydro-naphthalenic or anthracenic 1,4-endoperoxides in which other radical processes may compete with isomerization into diepoxides.On photolysis in benzene at long wavelengths, 1,4-epidioxy-1,4-dimethyl-1,2,3,4-tetrahydronaphthalene 4N undergoes mainly an isomerization into 1,8a:4,4a-diepoxy-1,4-dimethyl-1,2,3,4,4a,8a-hexahydronaphthalene 8N, along with a minor cleavage into ethylene and o.diacetylbenzene 10N.Similarly, 1,4-epidioxy-1,4-dimethyl-1,2,3,4-tetrahydroanthracene 4A leads to the hexahydroanthracenic diepoxide 8A and to 2,3-diacetylnaphthalene 10A.These rather unstable diepoxides rearrange spontaneously at room temperature into 2,5-epoxy-2,5-dimethyl-2,3,4,5-tetrahydro-benzo or naphthooxepines 11N and 11A.Their primary formation during photolysis was established by trapping with N-methylmaleimide, which adds on 8N in the 5,8 and on 8A in the 9.10 positions giving the corresponding syn adducts 9N and 9A, and by the isolation of diepoxide 8N at low temperature.Thermolysis of endoperoxides 4N and 4A by refluxing in high boiling solvents leads to very similar results.Photo-oxygenation of diepoxide 8N gives the isomeric 5,8-epidioxy-1,8a:4,4a-diepoxy-1,4-dimethyl-1,2,3,4,4a,5,8,8a-octahydronaphthalenes, syn 13 and anti 14 which can be photo-isomerized into 1,8a:4,4a:5,6:7,8-tetraepoxy-1,4-dimethyl-perhydronaphthalenes, respectively syn 15 and anti 16.
Reactions of Copper(II) Halides with Aromatic Compounds. Part XII. Reactions of 9-Methyl-10-phenylanthracene, 1,4,9-Trimethylanthracene, 9,10-Dimethylanthracene and 1,5-Dichloro-9-methylanthracene in Methanol.
Mancilla, Jerson M.,Nonhebel, Derek C.,Scullion, Ian
, p. 1601 - 1619 (2007/10/02)
The title compounds react with copper(II) bromide in methanol to give the corresponding 9-methoxymethyl compounds. 1,4,9-Trimethylanthracene and 1,5-dichloro-9-methylanthracene also gave 1,2-di-(1,4-dimethyl-9-anthryl)ethane (6) and 1,5-dichloro-9,10-dimethoxy-9,10-dihydroanthracene (9) respectively.The formation of all these products can be interpreted in terms of initial electron transfer oxidation of the substituted anthracene to its radical cation, which either subsequently loses a proton to give the substituted 9-anthrylmethyl radical or undergoes solvent capture.
