- Soluble Tetraaminotriptycene Precursors
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An efficient route to soluble triptycene tetraamines, shape-persistent molecules containing two ortho-phenylenediamine motifs, is reported. These tetraamines are stable, prepared in good yields, easily purified by column chromatography, and can be readily condensed to give a range of imidazole and pyrazine derivatives.
- White, Nicholas G.,MacLachlan, Mark J.
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- Synthesis, Structure, and Complexation Properties of a C3-Symmetrical Triptycene-Based Anion Receptor: Selectivity for Dihydrogen Phosphate
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A new anion binding motif based on triptycene core has been synthesized from 2,7,14-trinitrotriptycene. Its well-defined binding pocket allowed for the selective recognition and sensing of dihydrogen phosphate in DMSO-d6 + 0.5% H2O.
- Granda, Jaroslaw M.,Grabowski, Jakub,Jurczak, Janusz
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- THE ELECTRON SPIN RESONANCE OF THE RADICAL CATIONS OF P-TERPHENYL, TRIPHENYLENE AND TRIPTYCENE
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The ESR spectra of the radical cation of p-terphenyl (1), triphenylene (2), and triptycene (3) have been investigated in fluid solution. .The hyperfine coupling constants of 1+. are in line with those predicted on the simple Hueckel-McLachlan-McConnel model, and suggested that it is a simple near planar monomeric species.The radical cation from 2 formed an adduct with 2 and only the spectrum of the dimeric species 22+. could be detected.The ESR spectrum of 3+. is in accord with that predicted for the form of the SOMO, the bridgehesd protons showing only a very small hyperfine coupling.When 3+. is generated photolytically the presence of Hg(OCOCF3)2 or Tl(OCOCF3)3, the ESR spectra indicate that subsequent mercuration or thallation of 3+. occurs in the β-position.When AlCl3 is used as the reagent, 3+. can appereantly undergo a retro-Diels-Alder reaction, and the spectrum of 3+. becomes replaced by that of the anthracene radical cation.
- Courtneidge, John L.,Davies, Alwyn G.,McGuchan, Deborah C.
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- Microwave-induced covalent functionalization of few-layer graphene with arynes under solvent-free conditions
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A non-conventional modification of exfoliated few-layer graphene (FLG) with different arynes under microwave (MW) irradiation and solvent-free conditions is reported. The described approach allows reaching fast, efficient and mild covalent functionalization of FLG.
- Sulleiro,Quiroga,Pe?a,Pérez,Guitián,Criado,Prato
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supporting information
p. 2086 - 2089
(2018/03/06)
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- Anhydrous proton conduction in porous organic networks
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Solid electrolyte separators within fuel cells enable efficient charge transport and prevent a mass bypass between the two half cells. Hydrated systems, like Nafion, reach unprecedented proton conductivities at ambient temperatures, but the demanding humidity management prevents their use beyond 80 °C, hence limiting the efficiency of current polymer-based systems. As such, water free and chemically inert, solid materials with excellent conductivities between 100 °C and 200 °C, are of high interest. A promising approach is the incorporation of heavier amphoteric molecules into micro- and mesoporous frameworks. Stronger host-guest interactions allow for higher temperatures, while still maintaining sufficient mobility and efficient transport pathways. Here, we present a systematic study investigating the influence of porosity, framework topology and dimensionality as well as framework functionality and charge carrier uptake on the proton conductivity for six porous organic networks (PONs) loaded with imidazole via gas phase adsorption. The resulting materials were thoroughly characterized by multinuclear NMR and IR spectroscopy and physisorption as well as powder X-ray diffraction and DSC experiments, revealing homogeneous distribution of the amphoteric guests within the pore structure. Electrochemical impedance spectroscopy up to 130 °C revealed remarkable conductivities of up to 10?3 S cm?1 under anhydrous conditions. We found 3D networks to favour high imidazole loading leading to high proton conductivities based on the Grotthuss mechanism. In contrast, 2D networks showed a lower guest molecule uptake and thus lower proton conductivities, which were governed by vehicle transport. Additional acid/base functionalities within the frameworks seem to have a negative effect on the proton conduction.
- Klumpen,Winterstein,Papastavrou,Senker
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supporting information
p. 21542 - 21549
(2018/11/20)
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- Pseudocyclic Arylbenziodoxaboroles: Efficient Benzyne Precursors Triggered by Water at Room Temperature
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New organohypervalent iodine compounds, arylbenziodoxaborole triflates, were prepared from 1-acetoxybenziodoxaboroles and arenes by treatment with trifluoromethanesulfonic acid under mild conditions. Single crystal X-ray crystallography of these compounds revealed a pseudocyclic structure with a short intramolecular interaction of 2.698 to 2.717 ? between oxygen and iodine in the benziodoxaborole ring. These new pseudocyclic aryliodonium salts readily generate aryne intermediates upon treatment with water at room temperature. The generated aryne intermediates react with various substrates to give the corresponding aryne adducts in moderate to good yields. Furthermore, the new benzyne precursors can also work as arylating reagents towards aromatic rings. The aryne intermediates generated from arylbenziodoxaborole triflates selectively react with tert-butyl phenol forming products of ortho arylation in moderate yields.
- Yoshimura, Akira,Fuchs, Jonathan M.,Middleton, Kyle R.,Maskaev, Andrey V.,Rohde, Gregory T.,Saito, Akio,Postnikov, Pavel S.,Yusubov, Mekhman S.,Nemykin, Victor N.,Zhdankin, Viktor V.
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supporting information
p. 16738 - 16742
(2017/12/02)
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- 1,4-Selective Diels - Alder reaction of 9,10-diethynylanthracene with 3,6-difluorobenzyne
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Diels - Alder reaction of 9,10-bis(3-hydroxy-3-methyl-1-butynyl)anthracene with 3,6-difluorobenzyne yields the naphthobarrelene derivative via 1,4-addition of difluorobenzyne in a higher yield than the 9,10-adduct having a triptycene core. The DFT calculations revealed that the intermediate for the former reaction is stabilized more significantly by attractive interaction between a fluorine atom at the benzyne ring and a hydrogen atom at the anthracene ring.
- Tsuchido, Yoshitaka,Ide, Tomohito,Suzaki, Yuji,Osakada, Kohtaro
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supporting information
p. 821 - 823
(2015/06/25)
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- Integrating reaction and analysis: Investigation of higher-order reactions by cryogenic trapping
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A new approach for the investigation of a higher-order reaction by on-column reaction gas chromatography is presented. The reaction and the analytical separation are combined in a single experiment to investigate the Diels-Alder reaction of benzenediazonium-2-carboxylate as a benzyne precursor with various anthracene derivatives, i.e. anthracene, 9-bromoanthracene, 9-anthracenecarbox-aldehyde and 9-anthracenemethanol. To overcome limitations of short reaction contact times at elevated temperatures a novel experimental setup was developed involving a cooling trap to achieve focusing and mixing of the reactants at a defined spot in a fused-silica capillary. This trap functions as a reactor within the separation column in the oven of a gas chromatograph. The reac-tants are sequentially injected to avoid undefined mixing in the injection port. An experimental protocol was developed with optimized injection intervals and cooling times to achieve sufficient conversions at short reaction times. Reaction products were rapidly identified by mass spectrometric detection. This new approach represents a practical procedure to investigate higher-order reactions at an analytical level and it simultaneously provides valuable information for the optimization of the reaction conditions.
- Stockinger, Skrollan,Trapp, Oliver
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p. 1837 - 1842
(2013/10/22)
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- Auto-tandem catalysis: Synthesis of acridines by Pd-catalyzed C=C bond formation and C(sp2)-N cross-coupling
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A facile palladium-catalyzed synthesis of acridines has been realized by consecutive C=C double bond formation and C-N cross-coupling. A variety of functionalized acridines can be accessed from easily available o-dihalobenzenes and N-tosylhydrazones in a single operation. This one-pot protocol has a wide scope with respect to both coupling partners, and provides an efficient route to functionalized acridine derivatives, which are generally difficult to synthesize by previously known methods.
- Huang, Zhongxing,Yang, Yang,Xiao, Qing,Zhang, Yan,Wang, Jianbo
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supporting information
p. 6586 - 6593
(2013/01/15)
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- Microwave flash pyrolysis
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(Chemical Equation Presented) In a microwave reactor, graphite heats rapidly to high surface temperatures; applications of graphite thermal "sensitization" have been described previously. We report here that microwave thermal sensitization with graphite, carbon nanotubes, or silicon carbide can be used to carry out reactions more typically accomplished by flash vacuum pyrolysis (FVP) and which usually require temperatures much higher than the nominal limit of a microwave reactor. The graphite-sensitized microwave reaction of azulene in the solid phase at temperatures of 100 to 300°C affords rapid rearrangement to naphthalene, a reaction typically observed by FVP at 700-900°C. Multiwall carbon nanotubes give similar results when used as a thermal sensitizer. Other graphite-sensitized reactions that we have observed include the following: conversion of 2-ethynylbiphenyl to phenanthrene, fragmentation of phthalic anhydride to benzyne, cleavage of iodobenzene to phenyl radical, aryl-aryl bond cleavage, and a variety of cycloaromatizations. An advantage is seen for less volatile substrates. Rearrangement of azulene and generation of benzyne from phthalic anhydride have also been observed on powdered silicon carbide. Because of the high temperature, rapid heating, and frequent ejection of material from the irradiation zone, we refer to this general method as microwave flash pyrolysis (MFP).
- Hee, Yeon Cho,Ajaz, Aida,Himali, Dibya,Waske, Prashant A.,Johnson, Richard P.
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scheme or table
p. 4137 - 4142
(2009/09/25)
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- A study of BF3-promoted ortho lithiation of anilines and DFT calculations on the role of fluorine-lithium interactions
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(Figure Presented) Director's cut: The poor directing ability of the dimethylamino group in directed ortho metalation is altered by complexation to BF3, which makes it more strongly activating than methoxy and chloro groups. DFTcalculations of simplified lithiated intermediates reveal a small role of the inductive effect, but a distinctive F...Li interaction that leads to a F-Li distance which is remarkably similar to the C-Li distance.
- Kessar, Satinder V.,Singh, Paramjit,Singh, Kamal N.,Bharatam, Prasad V.,Sharma, Arvind K.,Lata, Sneh,Kaur, Amarjit
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supporting information; body text
p. 4703 - 4706
(2009/02/06)
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- Nucleophilic substitution induced by electron transfer at the bridgehead of polycyclic alkanes: Competition between polar and radical pathways
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A series of 2,5(or 1,4)-dihaloadamantanes (4 and 5, X = Y = halogens) and 9,10-dihalotriptycenes (7, X = Y = halogens) as well as two 5-halo (X) adamantan-2-ones (6, Y = O,X = Br and I) have been treated with Me3SnLi in THF in the absence and presence of tert-butylamine (TBA) and dicyclohexylphosphine (DCHP). The product distributions of these reactions have been established by 13C and 119Sn NMR spectroscopy, vapor-phase chromatographic analyses, and GC/MS. The former compounds (4 and 5) appear to react exclusively by a free-radical chain process (SRN1 mechanism) to yield tin substitution products. By contrast, the triptycenes react predominantly by a polar mechanism initiated by the formation of a carbanion. In the case of the halo ketones (6, Y = O,X = Br and I), a mechanistic divergence of the reaction was unexpectedly encountered. Whereas the bromo ketone provides the substitution product (6, Y = O,X = SnMe3) in good yield (ca. 75%), apparently by a radical pathway, the iodo ketone yields a fragmentation product (ca. 95% yield) by a polar mechanism. This mechanistic switch highlights the importance of the electronegativity of the leaving group as well as substituent-induced electron delocalization as molecular factors governing the competition between radical and polar pathways.
- Adcock,Clark,Trout
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p. 3362 - 3371
(2007/10/03)
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- A new and efficient hypervalent iodine-benzyne precursor, (phenyl)[o- (trimethylsilyl)phenyl]iodonium triflate: Generation, trapping reaction, and nature of benzyne
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A new and efficient hypervalent iodine-benzyne precursor, (phenyl)[2- (trimethylsilyl)phenyl]-iodonium triflate (10), is reported. The hypervalent iodine-benzyne precursor 10 is readily prepared by reaction of 1,2- bis(trimethylsilyl)benzene with a PhI(OAc)2/TfOH reagent system. Treatment of 10 with Bu4NF in CH2Cl2 at room temperature gives high yields of the benzyne adducts in the presence of a trapping agent such as furan, 2- methylfuran, anthracene, tetraphenylcyclopentadienone, or 1,3- diphenylisobenzofuran. Especially, the result of the reaction in the presence of furan indicates a quantitative generation of benzyne and its efficient capture by the furan. Similarly, methylbenzynes (22 and 27) are efficiently generated from the corresponding methyl-substituted (trimethylsilyl)phenyliodonium triflates (12 and 13). The preparation of the hypervalent iodine-benzyne precursors, the generation of benzynes, the trapping reactions, and the nature are described in detail together with the advantages of the present reagents over the previously reported benzyne precursors.
- Kitamura, Tsugio,Yamane, Masakatsu,Inoue, Kensuke,Todaka, Mitsuru,Fukatsu, Norihiko,Meng, Zhaohong,Fujiwara, Yuzo
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p. 11674 - 11679
(2007/10/03)
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- Synthesis of Precursors for the Pyrolytic Formation of Pentatetraenones
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3-(9',10'-Dihydro-9',10'-ethanoanthracen-11'-ylidene)prop-2-enoyl chloride and its [12',12'-2H2] and [1-13C] isotopomers have been prepared and pyrolysed. Argon matrix infrared spectroscopy showed ν2 bands at 2207.7, 2207.0, and 2168.5 cm-1 respectively for the three pentatetraenone isotopomers. The pyrolysate of the 12'-methyl substituted precursor showed a band at 2205 cm-1 which was tentatively assigned to methylpentatetraenone. The 12'-ethenyl substituted precursor gave a pyrolysate showing ketene bands but also yielded 9,10-dihydro-9,10[1',2']-benzenoanthracene.
- Arena, Phillip,Brown, Roger F. C.,Eastwood, Frank W.,McNaughton, Don
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p. 663 - 672
(2007/10/03)
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- A mild alternative to the use of benzyne in [4 + 2]-cycloaddition reactions
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A synthetic protocol to assemble a benzene ring, mimicking the [4 + 2]-cycloaddition of benzyne is reported. The sequence of reactons is made up of simple and mild steps and overall it furnishes comparable or even better yields with respect to the direct addition of benzyne.
- Cossu, Sergio,De Lucchi, Ottorino
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p. 14247 - 14252
(2007/10/03)
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- (Phenyl)iodonium Triflate. A New and Efficient Precursor of Benzyne
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(Phenyl)iodonium triflate readily prepared from o-bis(trimethylsilyl)benzene and the hypervalent iodine(III) reagent shows excellent formation of benzyne under mild and neutral conditions and efficiently provides adducts with typical trapping agents, e. g. furan, anthracene, diphenylisobenzofuran and tetraphenylcyclopentadienone.
- Kitamura, Tsugio,Yamane, Masakatsu
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p. 983 - 984
(2007/10/02)
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- Synthesis and cycloreversion of benzocyclobutene- and benzocyclobutadiene-anthracene adducts
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The [4+2]-cycloadducts of anthracene and benzocyclobutene or benzocyclobutadiene were synthesized and their cycloreversion was investigated.
- Okada,Kawai,Oda
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p. 257 - 260
(2007/10/02)
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- DECARBOXYLATIVE PHOTOOXYGENATION OF CARBOXYLIC ACIDS BY THE USE OF ACRIDINE
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A new method of decarboxylative photooxygenation of free carboxylic acids is developed by the use of acridine as a light absorber, leading to alcohols after reductive treatment of the photolysate.
- Okada, Keiji,Okubo, Katsura,Oda, Masaji
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- Reductive decarboxylation of N-(acyloxy)phthalimides via redox-initiated radical chain mechanism
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Highly efficient reductive decarboxylation of N-(acyloxy)phthalimides which are readily prepared from carboxylic acids was achieved by visible light irradiation using Ru(bpy)3Cl2 as a sensitizer in the presence of BNAH and t-BuSH via radical chain mechanism.
- Okada,Okubo,Morita,Oda
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p. 7377 - 7380
(2007/10/02)
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- Photochemie der 1-(Carbmethoxy-aryl)- und 1-(Carboxy-aryl)-3-(3-alkyl-benzthiazolinyliden-(2))-triazene als potentielle CEL-Farbstoffe
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1-(Carbmethoxy-aryl)-3-(3-alkyl-benzthiazolinyliden-(2))-triazenes (ester-triazenes) (1) were synthesized by coupling of substituted 3-alkyl-2-imino-benzthiazolines-(1,3) with 2-, 3- and 4-carbmethoxy-benzenediazonium salts.The Z-isomers obtained can be transformed into the E-isomers 2 photochemically or by heating.In the presence of acids the E-ester-triazenes are protonated.From the E-ester-triazenes the potassium-salts (4) can be produced by alkaline ester hydrolysis.With hydrochloric acid the E-triazene-potassium salts (4) can be produced by alkaline etser hydrolysis.With hydrochloric acid the E-triazene-potassium salts (4) can be transformed into the protonated (at the N(1)-Atom) E-acid-triazenes (5).Their photochemical properties are identical with those of the protonated E-ester-triazenes (3).The 1-(carboxy-aryl)-3-(3-alkylbenzothiazolinyliden-(2))-triazenes (E-acid-triazenes) (6) can be obtained from the protonated derivates by deprotonation in the presence of water.The photochemical behaviour of the E-acid-triazenes (6) and of the E-triazene-potassium-salts (4) depends on the position of the carboxy-group (2-position: photolysis, 3- and 4-position: photoisomerisation).The uv/vis-spectroscopical and photochemical properties of the triazene-derivates in solution and in polymeric layers are discussed.
- Fanghaenel, E.,Bauroth, J. U.,Hentschel, H.,Gussmann, F.,Alzyadi, H.,Ortmann, W.
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p. 241 - 247
(2007/10/02)
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- Net carbon atom loss from 5,6-(9′,10′-dihydro-9′,10′-anthraceno)-1,2,4,6- cycloheptatetraene
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The photolysis of the sodium salt of 4,5-(9′,10′-dihydro-9′,10′-anthraceno)-2,4,6- cycloheptatrien-1-one (13) in THF or the reaction of KO/-Bu with 1-chloro-4,5-(9′,10′ dihydro-9′,10′-anthraceno)-1,3,5-cycloheptatriene (14) in THF produced triptycene (2) in up to 30 % yield. Neither 1-triptycenyl carbene (7) nor 2-triptycenyl carbene (5) formed triptycene.
- McCarthy, Timothy J.,Pang, David C.,Tivakornpannarai, Supanna,Waali, Edward E.
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p. 6265 - 6268
(2007/10/02)
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- PHOTODECARBOXYLATION OF UNMODIFIED CARBOXYLIC ACIDS WITH USE OF AZA AROMATIC COMPOUNDS
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A very simple procedure for photodecarboxylation of intact carboxylic acids leading to alkanes is developed with use of aza aromatic compounds as light absorbers and t-BuSH as a hydrogen donor.
- Okada, Keiji,Okubo, Katsura,Oda, Masaji
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p. 6733 - 6736
(2007/10/02)
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- A NEW SOURCE FOR GENERATION OF BENZYNE AND PYRIDYNE: REACTIONS OF O-HALOPHENYL (OR 3-BROMO-4-PYRIDYL) PHENYL SULFOXIDES WITH GRIGNARD REAGENTS
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o-Chloro- and o-bromophenyl phenyl sulfoxides and (3-bromo-4-pyridyl) phenyl sulfoxide were treated with Grignard reagents to generate benzyne (or 3,4-pyridyne) in THF.The o-iodophenyl derivative, on the other hand, gave mainly o-(arylsulfinyl)phenyl Grignard reagent.
- Furukawa, Naomichi,Shibutani, Tadao,Fujihara, Hisashi
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p. 2727 - 2730
(2007/10/02)
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- CORRELATION OF THE TWO TORSIONAL DEGREES OF FREEDOM ABOUT THE BONDS CONNECTING THE BRIDGEHEAD CARBONS TO THE SULFUR ATOM IN BIS (9-TRIPTYCYL) SULFIDE
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Bis (9-triptycyl) sulfides were prepared by pyrolytic extrusion of sulfur dioxide from the corresponding thiosulfonates.A pair of torsional motions about the C-S bonds in these sulfides are in strict gearing and require a barrier of 29.3 kcal/mol for gear slippage.
- Kawada, Yuzo,Ishikawa, Joji,Yamazaki, Hiroshi,Koga, Gen,Murata, Shigeru,Iwamura, Hiizu
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p. 445 - 448
(2007/10/02)
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- SYNTHESIS OF 9,10-BIS(9-TRIPTYCYLOXY)TRIPTYCENES MOLECULAR DESIGN OF A SYSTEM WITH DOUBLY CORRELATED INTERNAL ROTATION
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Torsional motions around the two C-C and C-O bonds in di(9-triptycyl)methanes, Tp2CH2, and di(9-triptycyl) ethers, Tp2O, respectively, have a high barrier to uncorrelated rotation and a very low barrier to coupled disrotation.As a result, a new stereoisomerism is generated due to different phase relationships between appropriately labeled benzene rings, at least one on each Tp unit.To extend the concept and further demonstrate the high correlation in the torsional motions for these systems, a doubly geared molecule, 9,10-bis(3-chlorotriptycyloxy)triptycene (1), was conceived and constructed.Bis(3-chloro-9-triptycyl)9,10-triptycenebis(peroxycarboxylate) was prepared.The meso and dl isomers of 1 were separated by HPLC on microsilica.The structures were confirmed by high resolution (13)C-NMR spectra which revealed an interesting stereochemical feature: one benzene ring of the middle unsubstituted triptycene moiety is diastereotopic to the other two.The rates of isomerisation were measured in diphenylmethane solution to give the activation parameters for the gear slipping process: ΔH=42.1+/-1.3 kcal mol-1 and ΔS=-3.2+/-2.3 e.u.The significance of these findings as an extreme case for the dynamics of molecular chains is discussed.
- Koga, Noboru,Kawada, Yuzo,Iwamura, Hiizu
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p. 1679 - 1686
(2007/10/02)
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- Photostimulated Reaction of 1-Haloadamantane and 9-Bromotriptycene with Nucleophiles. A Nucleophilic Substitution by SRN1 at the Bridgehead Position
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1-Haloadamantanes and 9-bromotriptycene react under irradiation with diphenylphosphide and diphenylarsenide ions to give the substitution product in good yields. 1-Iodoadamantane (8) also reacts with disodium telluride and disodium selenide under irradiation to give di-1-adamantyl ditelluride and di-1-adamantyl diselenide, respectively. 9,10-Dibromotriptycene with diphenylphosphide gives a good yield of the disubstitution product.It seems that all these reactions occur by the SRN1 mechanism.Substrate 8 reacts under irradiation with carbanionic nucleophiles and diethyl phosphite ion, but the products are adamantane and 1,1'-biadamantyl rather than substitution products.These nucleophiles transfer an electron to 8 to form radical anions which fragment to 1-adamantyl radicals.The radicals are reduced or dimerized.In contrast, amide ions do not react with 8.The ease of the halogen nucleofugality is I > Br > Cl, the same as in the aromatic system.
- Palacios, Sara M.,Santiago, Ana N.,Rossi, Roberto A.
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p. 4609 - 4613
(2007/10/02)
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- High-Yield Direct Synthesis of a New Class of Tertiary Organolithium Derivatives of Polycyclic Hydrocarbons
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For the first time, 1- and 2-adamantyllithium, 1-diamantyllithium, 3,5,7-trimethyl-1-adamantyllithium, 1-twistyllithium, 3-methyl-7-noradamantyllithium, 1-triptycyllithium, and 3-homoadamantyllithium have been directly synthesized from the reaction of an organic halide and lithium metal.By use of certain experimental parameters, the phenomena at the metal-solution interface are controlled, thereby resulting in exceptionally high yields of this new class of organometallic compounds (>75percent, except in the case of 3-homoadamantyllithium).Competition between formation of the organometallic compound and formation of solvent-attack byproducts is determined by the degree of adsorption of the transient species (anion radical RX-. or radical pair R..Li) generated at the metal surface during attack by the halogenated derivative.
- Molle, G.,Bauer, P.,Dubois, J. E.
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p. 2975 - 2981
(2007/10/02)
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- Unconventional Synthesis and Conformational Flexibility of Bis(1-triptycyl) Ether
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The title compound was prepared by the thermolysis in perfluorodecalin of 1-triptycyl 1-triptyceneperoxycarboxylate which in turn was obtained by the reaction of 1-triptycyllithium with oxygen followed by treatment with 1-triptycenecarbonyl chloride.No sign of restricted rotation around the bridgehead-to-oxygen bonds of the ether was indicated by the 1H and 13C NMR spectra in spite of its overcrowded molecular framework.
- Kawada, Yuzo,Iwamura, Hiizu
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p. 2547 - 2548
(2007/10/02)
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