- The thermodynamic properties of thianthrene and phenoxathiin
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Measurements leading to the calculation of the standard thermodynamic properties are reported for thianthrene (Chemical Abstracts registry number ) and phenoxathiin (registry number ).Experimental methods included combustion calorimetry, adiabatic heat-capacity calorimetry, vibrating-tube densitometry, comparative ebulliometry, inclined-piston-gauge manometry, and differential-scanning calorimetry (d.s.c.).Critical properties were estimated for both materials based on the measurement results.Standard entropies, enthalpies, and Gibbs free energies of formation were derived for the gas for both compounds for selected temperatures between 298.15 K and 700 K.The property-measurement results reported here for thianthrene and phenoxathiin provide the first experimental gas-phase standard Gibbs free energies of formation for tricyclic diheteroatom-containing molecules.
- Steele, W. V.,Chirico, R. D.,Knipmeyer, S. E.,Nguyen, A.
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- Highly efficient CuOx/OMS-2 catalyst for synthesis of phenoxathiin derivatives via intramolecular arylations of phenols with aryl halides
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Phenoxathiin and its derivatives have attracted a great deal of interest due to their unique chemical and physical properties and their applications in fluorescent materials, antifungal activities and selective inhibitors. In the presence of copper supported on manganese oxide-based octahedral molecular sieves OMS-2 (CuOx/OMS-2), the heterogeneously catalytic synthesis of phenoxathiinan derivatives via intramolecular arylations of phenols with aryl bromide or aryl chloride has been achieved. TEM and XRD have confirmed the CuOx/OMS-2 catalyst has been successfully reused 8 times without a significant decrease in the yield, with simple filtration and washing as a means of separation.
- Liu, Na,Chao, Fei,Huang, Yu,Wang, Yanlan,Meng, Xu,Wang, Long,Liu, Xiang
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- Synthesis of phenoxathiins and phenothiazines by aryne reactions with thiosulfonates
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Novel synthetic methods for phenoxathiins and phenothiazines by aryne reactions are disclosed. We found that phenoxathiins were efficiently prepared by the reaction between aryne intermediates and S-(2-hydroxyaryl) 4-toluenethiosulfo-nates. A synthetic method for phenothiazines was also developed by the reaction of arynes with S-(2-aminoaryl) 4-toluenethiosulfonates.
- Hosoya, Takamitsu,Kanemoto, Kazuya,Sakata, Yuki,Yoshida, Suguru
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- Rh(III)-Catalyzed Direct ortho-Chalcogenation of Phenols and Anilines
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A highly efficient Rh(III)-catalyzed direct C-H chalcogenation of phenols and anilines has been achieved with the assistance of the 2-pyridyl group. The reaction features a broad substrate scope, good functional group tolerance, complete monothiolation selectivity, and easily removable directing group.
- Yang, Shiping,Feng, Boya,Yang, Yudong
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- Scalable electrochemical reduction of sulfoxides to sulfides
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A scalable reduction of sulfoxides to sulfides in a sustainable way remains an unmet challenge. This report discloses an electrochemical reduction of sulfoxides on a large scale (>10 g) under mild reaction conditions. Sulfoxides are activated using a substoichiometric amount of the Lewis acid AlCl3, which could be regeneratedviaa combination of inexpensive aluminum anode with chloride anion. This deoxygenation process features a broad substrate scope, including acid-labile substrates and drug molecules.
- Kong, Zhenshuo,Pan, Chao,Li, Ming,Wen, Lirong,Guo, Weisi
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supporting information
p. 2773 - 2777
(2021/04/21)
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- Arylation of aryllithiums with: S-arylphenothiazinium ions for biaryl synthesis
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Aryllithiums are one of the most common and important aryl nucleophiles; nevertheless, methods for arylation of aryllithums to produce biaryls have been limited. Herein, we report arylation of aryllithiums with S-arylphenothiazinium ions through selective
- Morofuji, Tatsuya,Yoshida, Tatsuki,Tsutsumi, Ryosuke,Yamanaka, Masahiro,Kano, Naokazu
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supporting information
p. 13995 - 13998
(2020/11/21)
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- Mo-Based Oxidizers as Powerful Tools for the Synthesis of Thia- and Selenaheterocycles
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A highly efficient synthetic protocol for the synthesis of thia- and selenaheterocycles has been developed. By employing a MoCl5-mediated intramolecular dehydrogenative coupling reaction, a broad variety of structural motifs was isolated in yields up to 94 %. The electrophilic key transformation is tolerated by several labile moieties like halides and tertiary alkyl groups. Due to the use of disulfide or diselenide precursors, a high atom efficiency was achieved.
- Franzmann, Peter,Beil, Sebastian B.,Schollmeyer, Dieter,Waldvogel, Siegfried R.
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p. 1936 - 1940
(2019/01/14)
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- HETERO-CYCLIC COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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Provided are a heterocyclic compound in a novel structure and an organic light emitting device comprising the same. A compound represented by chemical formula 1 can be used as a material for an organic layer in an organic light emitting device, thereby being capable of improving efficiency, having low driving voltage and/or improving lifespan properties of an organic light emitting device.COPYRIGHT KIPO 2018
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Paragraph 0187-190
(2018/04/18)
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- Transition-Metal-Free Suzuki-Type Cross-Coupling Reaction of Benzyl Halides and Boronic Acids via 1,2-Metalate Shift
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Cross-coupling of organoboron compounds with electrophiles (Suzuki-Miyaura reaction) has greatly advanced C-C bond formation and has been well received in medicinal chemistry. During the past 50 years, transition metals have played a central role throughout the catalytic cycle of this important transformation. In this process, chemoselectivity among multiple carbon-halogen bonds is a common challenge. In particular, selective oxidative addition of transition metals to alkyl halides rather than aryl halides is difficult due to unfavorable transition states and bond strengths. We describe a new approach that uses a single organic sulfide catalyst to activate both C(sp3) halides and arylboronic acids via a zwitterionic boron "ate" intermediate. This "ate" species undergoes a 1,2-metalate shift to afford Suzuki coupling products using benzyl chlorides and arylboronic acids. Various diaryl methane analogues can be prepared, including those with complex and biologically active motifs. The reactions proceed under transition-metal-free conditions, and C(sp2) halides, including aryl bromides and iodides, are unaffected. The orthogonal chemoselectivity is demonstrated in the streamlined synthesis of highly functionalized diaryl methane scaffolds using multi-halogenated substrates. Preliminary mechanistic experiments suggest both the sulfonium salt and the sulfur ylide are involved in the reaction, with the formation of sulfonium salt being the slowest step in the overall catalytic cycle.
- He, Zhiqi,Song, Feifei,Sun, Huan,Huang, Yong
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supporting information
p. 2693 - 2699
(2018/02/28)
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- Compound and organic electronic element comprising same
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The invention relates to a compound and an organic electronic element comprising the same. The compound disclosed in the invention is applied to the organic electronic element typified by organic light emitting elements, the driving voltage of the organic electronic elements can be lowered, optical efficiency can be improved, and lifetime characteristics of the elements can be improved via use of the thermal stability of the compound.
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Paragraph 0209-0211
(2017/11/29)
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- COMPOUND AND ORGANIC LIGHT EMITTING DEVICE COMPRISING THE SAME
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The present specification relates to a compound represented by chemical formula 1, and an organic light-emitting device comprising the same. The compound of the present specification may be used as a material for an organic material layer in an organic light-emitting device to improve efficiency, low driving voltage, and/or lifetime characteristic of the organic light-emitting device. Further, one embodiment of the present specification provides an organic light-emitting device which comprises: a first electrode; a second electrode facing the first electrode; and one or more organic material layers disposed between the first electrode and the second electrode, wherein at least one of the organic material layers comprises the compound of chemical formula 1.COPYRIGHT KIPO 2017
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Paragraph 0235-0239
(2018/02/10)
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- Cu-catalyzed synthesis of diaryl thioethers and S -cycles by reaction of aryl iodides with carbon disulfide in the presence of DBU
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Diaryl thioethers and S-cycles were obtained on the basis of the copper-catalyzed reaction of carbon disulfide and aryl iodides in the presence of DBU. This reaction enables the one-pot synthesis of diaryl thioethers by employing cheap, available, and easy-to-handle carbon disulfide with aryl iodides. The reaction was successfully employed in the construction of sulfur-containing cyclic molecules.
- Zhao, Peng,Yin, Hang,Gao, Hongxin,Xi, Chanjuan
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p. 5001 - 5006
(2013/06/27)
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- Regioselective synthesis of phenoxathiin derivatives under transition-metal-free conditions
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A simple and efficient method was developed for the synthesis of phenoxathiin derivatives. A range of 1,2-dihaloarenes or 1-halo-2-nitroarenes reacted with 2-sulfanylphenol to give the desired products in good-to-excellent yields. It is intriguing that 1-halo-2-nitroarenes containing electron-donating groups worked well as substrates in this reaction. Georg Thieme Verlag Stuttgart - New York.
- Hu, Fangdong,Zhao, Xin,Li, Yanqiu,Feng, Lei,Ma, Chen
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p. 966 - 970
(2013/05/09)
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- Synthetic routes to polyheteroacenes: Characterization of a heterocyclic ladder polymer containing phenoxathiinium-type building blocks
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The synthetic routes to ladder polymers that consist of benzenetetrayl subunits with oxo and methylsulfonio linkages are described. As the key intermediate, poly(phenylene oxide)s having pendant methylsulfenyl groups are prepared by copper-catalyzed oxidative polymerization of the corresponding phenols with O2. The oxidation of the polymer with an equimolar amount of H2O2 in the presence of acetic acid effects the high-yielding conversion of methylsulfenyl to methylsulfinyl groups without the formation of the undesired methylsulfonyl groups. The superacidified condensation of the resulting polymer (Swern reaction of aryl sulfoxides) under dilution conditions induces the polymer-analogous intramolecular electrophilic ring-closing reaction of the hydroxymethylphenylsulfonium cation onto the adjacent benzene ring to yield the required ladder polymer, which has proved to be a semiconductor with an intrinsic electric conductivity of 2 × 10-5 S/cm. A comparison of the spectroscopic properties of the ladder polymer with those of the model compounds such as 5-methylphenoxathiinium triflate and phenoxathiin discloses π-electron delocalization over the methylsulfonio linkages, demonstrating the efficacy of the ladderization for p-π/d-π interactions in arylsulfonium moieties. This synthetic approach permits the thio and alkylsulfonio ladder linkages for a variety of phenyl ethers to form in high yields.
- Oyaizu, Kenichi,Mikami, Takefumi,Mitsuhashi, Fumio,Tsuchida, Eishun
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- Phenoxathiin derivatives as inhibitors of monoamine oxidase
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PCT No. PCT/US97/23486 Sec. 371 Date Mar. 11, 1999 Sec. 102(e) Date Mar. 11, 1999 PCT Filed Aug. 19, 1997 PCT Pub. No. WO98/12190 PCT Pub. Date Mar. 26, 1998The present invention provide phenoxathiin compounds useful in the prophylaxis and treatment of mental disorders, such as depression. The present invention also provides a method for treating a mammal having depression, anxiety or other conditions responsive to inhibition of MAO-A. A method of preparing the compounds of the present invention is also provided.
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- Utilisations synthetiques d'une electrode soluble au soufre. III. Creation de l'enchainement C-S-C a partir d'ethers aromatiques et de phenols
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Use of a sacrificial sulfur electrode in electroorganic chemistry.III.Formation of the C-S-C bond from aromatic ethers and phenols.At a working potential of about +2.2 V (vs SCE) the carbon-sulfur electrode is a source of the electrogenerated cation S2+ in organic media.This electrophile can react with aromatic ethers and phenols to produce the corresponding monosulfides.This reaction may be regioselective. carbon-sulfur electrode / sacrificial electrode /sulfur cation / organic sulfide / electrophilic substitution
- Elothmani, Driss,Do, Quang Tho,Simonet, Jacques,Guillanton, Georges Le
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p. 779 - 788
(2007/10/02)
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- Formation of Benzoxathiete under Mild Conditions and Its Valence Tautomerism in Solution to Monothio-o-benzoquinone: An Experimental and Quantum Chemical Study
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Aprotic diazotization of 2-aniline in dimethoxyethane affords products that include biphenylene and dibenzo-1,4-oxathiane.Detection of these products is consistent with the formation of benzoxathiete and the valence tautomerism to monothio-o-benzoquinone with concomitant formation of dehydrobenzene by a competing pathway.The latter was independently trapped with 1,3-diphenylisobenzofuran and with 9,10-dimethylanthracene.The requirement for SO group participation in the formation of benzoxathiete is established by comparison with the behavior of the analogous thioether and sulfone compounds.EPR and spin-trapping experiments confirm the intermediacy of both oxygen- and nitrogen-centered free radicals which is consistent with the homolytic pathways proposed for the diazotization process.Parallel aqueous diazotization of 2-aniline affords vinyl acetate, phenol, and halobenzene consistent with the generation of dehydrobenzene but not benzoxathiete under these conditions.Spin-trapping/EPR studies gave no evidence for free-radical components in the protic diazotization reaction.Ab initio calculations using the 3-21G* and 6-31G* basis sets within the Hartree-Fock approximation, as well as the MP2/3-21G* method, predict an energetically feasible tautomerism of benzoxathiete to monothio-o-benzoquinone.The 3-21G* calculations reveal the presence of a biradical intermediate for this reaction which, as a singlet, features an energy higher than the benzoxathiete by 33 kcal/mol, while as the corresponding triplet it proves to be lower in energy than the benzoxathiete by 2.5 kcal/mol.This process, however, might be symmetry forbidden.By contrast, the symmetry-allowed cycloreversion pathway of benzoxathiete to dehydrobenzene and SO is energetically much less favorable.
- Naghipur, Ali,Reszka, Krzysztof,Sapse, Anne-Marie,Lown, J. William
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p. 258 - 268
(2007/10/02)
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- New Reagents 7: Facile Reduction of Sulphoxides to Sulphides Using Aluminium Chloride - Sodium Iodide System
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Sulphoxides are reduced to the corresponding sulphides in good to excellent yields with aluminium chloride - sodium iodide system.Although the system bears similarity to aluminium iodide, closer study reveals distinct differences.
- Bhatt, Vivekananda M.,Babu, Ramesh J.
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p. 259 - 260
(2007/10/02)
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- ARENE COMPLEXES OF TRANSITION METALS IN REACTIONS WITH NUCLEOPHILIC REAGENTS. XI. SYNTHESIS OF HETEROCYCLIC COMPOUNDS BY NUCLEOPHILIC SUBSTITUTION OF CHLORINE ATOMS IN η6-o-DICHLOROBENZENECHROMIUM TRICARBONYL
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A method was developed for the synthesis of dibenzo-1,4-dioxin, phenoxazine, and phenoxathiin and also their chromium tricarbonyl complexes by the reaction of η6-o-dichlorobenzenechromium tricarbonyl with the alkali-metal salts of pyrocatechol, o-aminophenol, and o-mercaptophenol in HMPTA.The composition of the reaction products and the yield of the heterocyclic compounds depend significantly on the nature of the solvent, the nucleophile, the condensing agent, and the reaction conditions.
- Litvak, V. V.,Goryunov, L. I.,Shteingarts, V. D.
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p. 138 - 144
(2007/10/02)
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- Synthesis and Some Heterocyclic Systems from Nucleophilic Substitution Reactions with η6-o-Dichlorobenzene-η5-cyclopentadienyliron Hexafluorophosphate
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A method for the synthesis of heterocyclic systems related to 9,10-dihydroanthracene with two hetero-atoms at the 9,10-positions is described.It involves the nucleophilic substitution reaction of η6-o-dichlorobenzene-η5-cyclopentadienyliron hexafluorophosphate with two nucleophilic groups (OH, SH and/or NH2) located in the 1,2-positions of a benzene ring to give a cyclopentadienyliron complexed heterocycle.Upon pyrolytic sublimation of the complex, the free heterocyclic compound is then obtained.
- Sutherland, Ronald G.,Piorko, Adam,Gill, Udai S.,Lee, Choi Chuck
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p. 801 - 803
(2007/10/02)
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- Ion Radicals. 46. Reactions of the Adducts of Thianthrene and Phenoxathiin Cation Radicals and Cyclohexene with Nucleophiles
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Thianthrene cation radical perchlorate 1a reacts with cyclohexene to give an adduct .Reactions of 2a with CN-, C6H5S-, and I- have been studied in dimethyl sulfoxide (Me2SO) and ethanol at room temperature.Reaction of the analogous adduct of cyclohexene and phenoxathiin cation radical perchlorate 2b with I- in ethanol was also studied.The reactions indicate that the adducts have the trans-1,2 structure and undergo facile substitution (SN2) and subsequent elimination (E2) reactions at room temperature.
- Iwai, Kiyoshi,Shine, Henry J.
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p. 271 - 276
(2007/10/02)
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- ESR Investigation of Radical Cations Formed from Aromatics and Heteroaromatics Adsorbed on Mo-Al2O3 Surfaces
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Molybdena-alumina is an important model catalyst system that has attracted considerable attention over the years.The behavior of adsorbed species on catalytic surfaces is also of interest because this may lead to a better understanding of the reaction mechanisms involved in the catalytic process.Using electron spin resonance, we have continued our systematic study of the molybdena-alumina system to which various aromatics and heteroaromatics have been added.We have investigated electron-transfer reactions with the molybdena-alumina surface and have also investigated the structural and dynamical aspects of the resulting adsorbed cations.Computer fitting of the cation ESR spectra has been carried out for a more precise determination of spectral parameters, and a comparison with solution spectral parameters has also been made.
- Petrakis, L.,Meyer, P. L.,Jones, Gerald L.
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p. 1029 - 1038
(2007/10/02)
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- THE DEOXYGENATION OF SULFOXIDES WITH ANHYDROUS HCl/KI
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Dialkyl and diaryl sulfoxides can be deoxygenated to their corresponding sulfides in high yields and purity by using anhydrous HCl and KI in chloroform.The reaction is not accompanied by reductive chlorination.
- Chasar, Dwight W.,Shockcor, John P.
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p. 187 - 188
(2007/10/02)
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