- Synthesis of Heterocycle-Containing 9,9-Diarylfluorenes Using Superelectrophiles
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A superacid-promoted method for the synthesis of 9,9-diarylfluorenes is described. The chemistry involves cyclizations and arylations with biphenyl-substituted heterocyclic ketones and a mechanism is proposed involving superelectrophilic intermediates. The key reactive intermediates-dicationic and trication fluorenyl cations have been observed by low-temperature NMR and the mechanism has been further studied using DFT calculations.
- Gasonoo, Makafui,Sumita, Akinari,Boblak, Kenneth N.,Giuffre, Kristen,Ohwada, Tomohiko,Klumpp, Douglas A
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- The Argon Laser-Jet Initiated, Multiple-Photon (Reluctant), Electrocyclic Ring Opening of 10,10-Diphenyl-9-(10H)-phenanthrenone: A Carbene and Biradical Modeling Study.
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While 10,10-diphenyl-9-(10H)-phenanthrenone (1) is inert under conventional irradiation conditions, it undergoes decarbonylation under high-intensity argon laser-jet conditions to form 9,9-diphenylfluorene (3) and the cycloheptatriene 4.Molecular modeling studies indicate that 3 arises from collapse of the singlet carbene 15 and the triene 4 from the triplet carbene 35.
- Wilson, R. Marshall,Romanova, Tatiana N.,Azadnia, Ardeshir,Bauer, Jeanette A. Krause,Johnson, Richard P.
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Read Online
- Compound constituting a hole transfer layer and an electron transfer layer of an organic light emitting diode or a method for producing the same
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The present invention relates to a compound constituting a hole transport layer and an electron transport layer of an organic light emitting diode, or a method for manufacturing the same. According to the present invention, it is possible to provide a plurality of compounds having excellent yields and excellent purity constituting the hole transport layer and the electron transport layer. An object of the present invention is to provide the compound constituting the hole transport layer and the electron transport layer of the organic light emitting diode, or the method for manufacturing the same.(AA) HPLC analysis result of a final productCOPYRIGHT KIPO 2020
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Paragraph 0034-0045
(2020/09/16)
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- Synthesis of spirocyclic diarylfluorenes by one-pot twofold SNAr reactions of diaryl sulfones with diarylmethanes
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Treatment of dibenzothiophene dioxides with cyclic diarylmethanes in the presence of KN(SiMe3)2 results in the formation of fluorene-based spirocyclic tetraarylmethanes in a single operation. The transformation would proceed via an intermolecular SNAr reaction of the dioxides with cyclic diarylmethylpotassium followed by intramolecular SNAr cyclization. This straightforward strategy provides a wide range of spirocyclic diarylfluorenes including unusual ones that are otherwise difficult to synthesize.
- Bhanuchandra,Yorimitsu, Hideki,Osuka, Atsuhiro
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supporting information
p. 384 - 387
(2016/02/19)
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- Palladium-catalyzed arylation of methylene-bridged polyarenes: Synthesis and structures of 9-arylfluorene derivatives
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In the presence of a catalytic system comprised of palladium(II) acetate and tricyclohexylphosphine, the reaction of fluorene with haloarenes generated 9-arylfluorenes in good to excellent yields. The scope and limitations of the coupling reaction were investigated. This synthetic protocol is more efficient than conventional methods. A wide range of functional groups, including alkyl, alkoxy, ester, and nitrile, can tolerate the reaction conditions herein. Sterically congested haloarenes also gave satisfactory results. Furthermore, this synthetic method is utilized to prepare 9,9-diarylfluorenes and tetraarylindenofluorene. Depending on the reaction conditions, the arylation of bowl-shaped sumanene gave monoarylated sumanene either as the sole product or with another diaryl-substituted product. Copyright
- Chen, Jheng-Jhih,Onogi, Satoru,Hsieh, Ya-Chu,Hsiao, Chien-Chi,Higashibayashi, Shuhei,Sakurai, Hidehiro,Wu, Yao-Ting
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experimental part
p. 1551 - 1558
(2012/07/17)
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- Non-catalytic conversion of C-F bonds of benzotrifluorides to C-C bonds using organoaluminium reagents
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A facile method for the conversion of C-F bonds of benzotrifluorides to C-C bonds has been developed using aluminium reagents in the absence of catalysts.
- Terao, Jun,Nakamura, Misaki,Kambe, Nobuaki
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supporting information; experimental part
p. 6011 - 6013
(2010/11/16)
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- A general and efficient synthesis of substituted fluorenes and heterocycle-fused indenes containing thiophene or indole rings utilizing a Suzuki-Miyaura coupling and acid-catalyzed Friedel-Crafts reactions as key steps
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A general and efficient synthesis of fluorenes or heterocycle-fused indenes including 3-thia-cyclopenta[a]indenes, 9-thia-indeno[1,2-a]indenes, 5,6-dihydroindeno[2,1-b]indoles has been developed. This methodology is realized by a multistep protocol involv
- Li, Guijie,Wang, Erjuan,Chen, Haoyi,Li, Hongfeng,Liu, Yuanhong,Wang, Peng George
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p. 9033 - 9043
(2008/12/22)
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- Syntheses and Reactions of 9-Substituted 10-Phenylthioxanthenium Salts: Negative Evidence for Thia-anthracene Oligomerisation
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Various 9-aryl-10-phenylthioxanthenium salts have been prepared and their stereochemistry determined by (1)H n.m.r. spectroscopy.Reactions of the 10-phenylthioxanthenium salts or 10-phenyl-10-thia-anthracenes with aryl-lithiums have been studied in order to investigate whether or not 10-thia-antracenes cause oligomerisation.The 10-phenylthioxanthenium salts reacted with aryl-lithiums to give 9-phenylthioxanthenes in good yields.However, 10-phenylthioxanthenium salt (19) when treated with phenyl-lithium at -15 to -20 deg C gave 9-phenylthioxanthenol (38) (17percent) together with 9-phenylthioxanthene (13) because of the lability of 10-phenyl-10-thia-anthracene to air. 10-Phenyl-9-(p-tolyl)-10-thia-anthracene (50) generated in situ from the sulphonium salt (22) and lithium diisopropylamide failed to react with p-tolyl-lithium.An isolable ylide, 9-benzoyl-10-phenyl-10-thia-anthracene (52) was treated with p-tolyl-lithium at 0 deg C to give 9-benzoylthioxanthene (4) (82percent).In contrast, 9,9,10-triphenylthioxanthenium salt (24) on treatment with phenyl-lithium gave a ring-opened product (40), a ring-contracted product (41), diphenylsulphide (42), and 9,9-diphenylthioxanthene (12).These results indicate that the 10-phenyl-thia-anthracenes or the ?-sulphuranes of thioxanthenes do not cause oligomerisation.
- Hori, Mikio,Kataoka, Tadashi,Shimizu, Hiroshi,Ikemori, Megumi,Aoyama, Yasuko
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p. 1209 - 1218
(2007/10/02)
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- REACTION OF TRIPHENYLMETHYLCATION IN TRIFLUOROMETHANESULFONIC ACID. REACTION OF CARBODICATIONS
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Triphenylmethyl cation reacts in the presence of trifluoromethanesulfonic acid in benzene.Products are 9-phenylfluorene, 9,9-diphenylfluorene, and triphenylmethane.A protonated triphenylmethyl cation and a protonated 9-phenylfluorenyl cation are postulated as intermediates.
- Ohta, Toshiharu,Shudo, Koichi,Okamoto, Toshihiko
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- REGIOSELECTIVE DIMETALLIERUNG VON AROMATEN. BEQUEMER ZUGANG ZU 2,2'-DISUBSTITUIERTEN BIPHENYLDERIVATEN
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Lithiation of biphenyl with 2.4 mol of n-butyllithium in the presence of TMEDA led directly to the 2,2'-dilithio derivative (I) in modest, but preparatively useful yields.I, in turn, was converted to a variety of products.The activation of the 2'-position of 2-lithiobiphenyl was shown directly by a separate experiment.MNDO calculations indicate stabilization in I by double bridging and in 2-lithiobiphenyl by intramolecular ? interaction of Li with the o-phenyl group.Similar interactions in substitution transition states rationalize the specificity of the reactions observed.
- Neugebauer, Wolfgang,Kos, Alexander J.,Schleyer, Rague
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p. 107 - 118
(2007/10/02)
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