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Henry J Shine - One of the best experts on this subject based on the ideXlab platform.
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an overview of some reactions of Thianthrene cation radical products and mechanisms of their formation
Journal of Sulfur Chemistry, 2006Co-Authors: Paramashivappa Rangappa, Henry J ShineAbstract:A comprehensive review of recent chemistry of Thianthrene cation radical is presented. Particularly, products and mechanisms of their formation from reactions with azo compounds, hydrazones, oximes, sulfonamides, alcohols, phenols, alkenes, alkynes and organometallics are discussed. Also, reactions of 5-(substituted)thianthrenium salts are reviewed.
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reaction of Thianthrene and phenoxathiin cation radicals with 2 3 dimethyl 2 butene chemical and electrochemical studies
Journal of Organic Chemistry, 2006Co-Authors: Bing Jun Zhao, Dennis H Evans, Norma A Maciasruvalcaba, Henry J ShineAbstract:Thianthrene cation radical tetrafluoroborate (Th•+BF4-) has been found to add to 2,3-dimethyl-2-butene (DMB) at 0 °C and −15 °C. The adduct, 2,3-dimethyl-2,3-(5,10-thianthreniumdiyl)butane ditetrafluoroborate (12), was isolated at −15 °C, and its 1H NMR spectrum was recorded at that temperature. The adduct was stable in CD3CN solution at −15 °C but decomposed slowly at 0 °C and quickly at 23 °C, forming the salt of 2,4,4,5,5-pentamethyl-2-oxazoline (8) with loss of Thianthrene (Th). These results explain why earlier attempts to prepare 12 and detect its formation at room temperature with NMR spectroscopy were not successful. Reaction of Th•+ with DMB was followed with cyclic voltammetry and was found to exhibit redox catalysis in which Th was regenerated. With the faster scanning techniques of cyclic voltammetry, the formation of 12 was detectable, with a reduction potential of about −1.0 V at 25 °C and 3 °C. The observed reduction potential was in harmony with reduction potentials of a number of other, s...
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adducts of Thianthrene and phenoxathiin cation radical tetrafluoroborates to 1 alkynes structures and formation of 1 5 thianthreniumyl and 1 10 phenoxathiiniumyl alkynes on alumina leading to α ketoylides and α ketols
Journal of Organic Chemistry, 2005Co-Authors: Paramashivappa Rangappa, Henry J Shine, John N Marx, Teyeb Ouldely, And Anna T Kelly, Kenton H WhitmireAbstract:[structure: see text] Thianthrene cation radical tetrafluoroborate (Th*+ BF4(-)) added to the terminal alkynes 1-pentyne, 1-hexyne, 1-heptyne, 1-octyne, 1-nonyne, and 1-decyne to form trans-1,2-bis(5-thianthreniumyl)alkene tetrafluoroborates (1-6). Similarly, addition of phenoxathiin cation radical tetrafluoroborate (PO*+ BF4(-)) to the same alkynes gave 1,2-bis(10-phenoxathiiniumyl)alkene tetrafluoroborates (7-12). The trans configuration of two of the adducts (1 and 4) was shown with X-ray crystallography. When solutions of 1-6 in chloroform were stirred with activated alumina, cis elimination of a proton and Thianthrene (Th) occurred with the formation of 1-(5-thianthreniumyl)alkyne tetrafluoroborates (1a-6a). Similar treatment of 8-12 caused elimination of a proton and phenoxathiin (PO) with formation of 1-(10-phenoxathiiniumyl)alkene tetrafluoroborates (8a-12a). Stirring of 1a-6a with alumina for short periods of time caused their conversion into 5-[(alpha-keto)alkyl]thianthrenium ylides (1b-6b) and alpha-ketols, RC(O)CH2OH (1c-6c).
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adducts of Thianthrene and phenoxathiin cation radical salts with symmetrical alkynes structure and formation of cumulenes on alumina leading to α diketones α hydroxyalkynes and α acetamidoalkynes
Journal of Organic Chemistry, 2005Co-Authors: Henry J Shine, Paramashivappa Rangappa, John N Marx, Dennis C Shelly, Teyeb Ouldely, Kenton H WhitmireAbstract:Thianthrene cation radical tetrafluoroborate (Th•+BF4-) added to 2-butyne, 3-hexyne, 4-octyne, and 5-decyne in MeCN to form trans bisadducts R(Th+)CC(Th+)R, where R = Me, Et, Pr, Bu (7a−d). Phenoxathiin cation radical tetrafluoroborate (PO•+BF4-) added similarly to the last three alkynes to form adducts R(PO+)CC(PO+)R, 8b−d. Cyclic monoadducts were not found. The trans structures of 7 and 8 were deduced with X-ray crystallography (7c) and NMR spectroscopy. When solutions of adducts in CHCl3 and MeCN were deposited on activated alumina, elimination of Thianthrene (Th) and phenoxathiin (PO) occurred almost quantitatively. Detailed studies with (7b−d) indicated that a cumulene (15) was formed by the elimination of Th and that 15 was subsequently converted into small amounts of other products. In CHCl3, these products were the respective alkyne, Thianthrene 5-oxide, an α-diketone (11), an α-hydroxyalkyne (12), and hydrogen. The same products were formed in MeCN along with an α-acetamidoalkyne (13). The format...
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decomposition of alkene adducts of Thianthrene cation radical in nitrile solvents formation of alkyl 2 oxazolines and a new class of four component products 5 1 alkoxyalkylidene ammonio alkylthianthrenium diperchlorates
Journal of Organic Chemistry, 2004Co-Authors: Henry J Shine, John N Marx, Teyeb Ouldely, Bing Jun Zhao, Kenton H WhitmireAbstract:The monoadducts (4a−d) of Thianthrene cation radical perchlorate (1a) and isobutene, 2-methylbutene, 2-methyl-2-butene, and 2-methylpentene decompose spontaneously in acetonitrile (MeCN) solution, with the formation of Thianthrene (Th). Decomposition of 4a (1,2-(5,10-thianthreniumdiyl)-2-methylpropane diperchlorate) and 4a‘, the corresponding dihexafluorophosphate, was studied in depth and extensively with 1H and 13C NMR spectroscopy. Decomposition of 4a was found to involve the solvent itself as well as water in the solvent, remaining from incomplete drying, and gave, apart from Th, successively, the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7). These salts, 6-HClO4 and 7-HClO4, respectively, were prepared and used in understanding the reactions of 4a as well as the relationships among 6, 7, and 2-(acetylamino)-2-methyl propanol (8) in acidified MeCN solution. Decompositions of 4a−d in MeCN and other nitriles (RCN) containing an added alcohol (R‘OH) led to n...
Seung Rim Shin - One of the best experts on this subject based on the ideXlab platform.
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synthesis of 2 2 3 and 4 pyridyl benzoxazoles by the reaction of phenolic schiff bases with Thianthrene cation radical
Journal of Heterocyclic Chemistry, 2002Co-Authors: Myeong Soon Park, Koon Ha Park, Kun Jun, Seung Rim ShinAbstract:2-(2-, 3-, and 4-Pyridyl)benzoxazole derivatives were prepared in excellent yields by the oxidative cyclization of phenolic Schiff bases with Thianthrene cation radical perchlorate in the presence of 2,6-di-tert-butyl-4-methylpyridine.
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2-Benzothiazolylhydrazones with Cation Radicals in Nitrile Solvents. Formations of 1,2,4-Triazoles and Triazolo[3,4-b]benzothiazoles
2000Co-Authors: Koon Ha Park, Kun Jun, Seung Rim ShinAbstract:Arenealdehyde 2-benzothiazolylhydrazone in Thianthrene cation radical afforded triazolo[3,4-b]benzothiazoles and 1,2,4-triazoles as major and minor product, respectively. On the contrary the similar reaction in tris(2,4-dibromophenyl)aminium hexachloroantimonate gave 1,2,4-triazoles and triazolo[3,4-b]benzothiazoles as ma-jor and minor product, respectively
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s triazolo 3 4 α phthalazines from 1 phthalazinylhydrazones by Thianthrene cation radical perchlorate
Synthetic Communications, 1999Co-Authors: Koon Ha Park, Kun Jun, Seung Rim ShinAbstract:Abstract 1-Phthalazinylhydrazones 4 gave i,-triazolo[3,4-a]phthalazines 5 in 94-98% yields by Thianthrene cation radical perchlorate (Th+′C104 -).
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2 arylbenzoxazoles from phenolic schiff s bases by Thianthrene cation radical
ChemInform, 1997Co-Authors: Kihun Park, Kun Jun, Seung Rim ShinAbstract:Abstract 2-Arylbenzoxazoles 2 have been made in 91–97% yields from phenolic Schiff's bases 1 by Thianthrene cation radical perchlorate (Th +. ClO 4 − ) in the presence of 2,6-di- tert -butyl-4-methylpyridine.
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cation radicals with 2 pyridylhydrazones in nitrile solvents s triazolo4 3 alpha pyridines by Thianthrene cation radical perchlorate and 1 2 pyridyl 1 2 4 triazol by tris 2 4 dibromophenyl aminium hexachloroantimonate
Bulletin of The Korean Chemical Society, 1997Co-Authors: Koon Ha Park, Kun Jun, Seung Rim ShinAbstract:Reactions of arenealdehyde 2-pyridylhydrazones (1) with Thianthrene cation radical () and tris(2,4-dibromophenyl)aminium hexachloroantimonate () were investigated. The major product was switched depending on the cation radical being used. That is, s-triazolo[4,3-α]pyridines (2), an intramolecular cyclization product, and 1-(2-pyridyl)-1,2,4-triazoles (3), an intermolecular cycloaddition product, were obtained as a major product when reacted with and , respectively in nitrile solvents. The plausible mechanisms are proposed based on both the reduction potentials of and and control experiments.
Juozas V Grazulevicius - One of the best experts on this subject based on the ideXlab platform.
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oxygen sensing properties of Thianthrene and phenothiazine derivatives exhibiting room temperature phosphorescence effect of substitution of phenothiazine moieties
Sensors and Actuators B-chemical, 2021Co-Authors: Karolis Leitonas, Ausra Tomkeviciene, Gabriel Baratte, Asta Dabuliene, Sanjay Madhuran Punniyakoti, Dmytro Volyniuk, Juozas V GrazuleviciusAbstract:Abstract Four new derivatives of Thianthrene and phenothiazine are reported as emitters for oxygen sensing. They exhibit both fluorescence and phosphorescence at room temperature. Effects of the substitution pattern of phenothiazine moiety on the thermal, electrochemical, emissive and oxygen sensing properties of the compounds are discussed. No phosphorescence at room-temperature was detected for deoxygenated solutions of the compounds. Room temperature phosphorescence of the different intensity was detected for the compounds being in crystalline or amorphous phase and for their dispersions in different polymeric matrices. Fast oxygen response (ca. 0.1 s) of room temperature phosphorescence was observed for only 1 wt.% of the dispersions in polymeric host. The highest oxygen sensitivity, was demonstrated for methylphenothiazinyl-disubstituted Thianthrene dispersed in poly(methyl methacrylate). Stern-Volmer constant of 21·10−4 ppm−1 was obtained compared to those of 0.97·10−4, 1.22·10−4 and 2.1·10−4 ppm−1 observed for the dispersions of other compounds. Displaying possibility of oxygen detection by different chromaticity responses of emission of the developed compounds, strong yellowish-green emission with CIE1931 coordinate of (0.294, 0.503) was observed for one sample in the absence of oxygen; while, weak deep-blue emission with CIE1931 coordinate of (0.174, 0.141) was observed for the same sample in oxygen atmosphere.
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bipolar Thianthrene derivatives exhibiting room temperature phosphorescence for oxygen sensing
Dyes and Pigments, 2019Co-Authors: Ausra Tomkeviciene, Juozas V Grazulevicius, Asta Dabulienė, Tomas Matulaitis, Matas Guzauskas, Viktorija Andruleviciene, Yuri Yamanaka, Yoshio Yano, Toshikazu OnoAbstract:Abstract The series of donor-acceptor (D-A) compounds consisting of a Thianthrene donor and either a benzophenone or a diphenylsulfone acceptor units were designed and synthesized via Suzuki cross-coupling. By varying the number of donor units, as well as by introducing heavy atom (Br) into the molecular structure the impact of these substituents on the thermal, electrochemical and emissive properties of the compounds was studied. The compound containing two Thianthrene units appeared to have higher thermal stability and higher glass transition temperature than monosubstituted derivative. All thianthrenyl substituted benzophenone or diphenylsulfone compounds showed bipolar behavior. Strong room temperature phosphorescence and dual fluorescence-phosphorescence were observed at room temperature. The compounds containing stronger electron acceptor diphenylsulfone demonstrated a two-fold higher photoluminescence quantum yield values up to 19% in rigid Zeonex® films than that benzophenone derivatives. The crystals of some synthesized compounds demonstrated oxygen sensing ability.
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Thianthrene and acridan substituted benzophenone or diphenylsulfone effect of triplet harvesting via tadf and phosphorescence on efficiency of all organic oleds
Organic Electronics, 2019Co-Authors: Ausra Tomkeviciene, Tomas Matulaitis, Matas Guzauskas, Viktorija Andruleviciene, Dmytro Volyniuk, Juozas V GrazuleviciusAbstract:Abstract Two new asymetric D–A–D′ type compounds containing benzophenone and diphenylsulfone as electron accepting core, and acridan and Thianthrene as electron donating moieties were design as multifunctional materials. The influence of different acceptor and donor units on thermally activated delayed fluorescence and room temperature phosphorescence was investigated and discussed. The combination of different donors with benzophenone unit resulted in the compound with effective frontier orbital separation, as well as the sustainment of high radiative rate. These statements are both experimentally and theoretically supported using time-resolved photoluminescence spectroscopy and DFT calculations. Deoxygenation experiment revealed higher triplet exciton contribution in the emission of benzophenone derivative, as compared to that of diphenylsulfone-based compound. The films of molecular mixtures of these emitters with 1,3-bis(N-carbazolyl)benzene demonstrated temperature-dependent photoluminescence. The estimated energy gaps between the lowest singlet and triplet states were found to be 0.06 eV and 0.27 eV for benzophenone and diphenylsulfone derivatives, respectively. Due to the relatively high singlet-triplet energy splitting of the diphenylsulfone-based compound, triplet harvesting was detected not only via temperature-stimulated fluorescence but also via room temperature phosphorescence. Displaying effect of triplet harvesting on efficiency of all-organic blue and green OLEDs based on Thianthrene and acridan-substituted benzophenone or diphenylsulfone derivatives demonstrated very different maximum external quantum efficiencies of 1.4 and 22.2% respectively.
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observation of dual room temperature fluorescence phosphorescence in air in the crystal form of a Thianthrene derivative
The Journal of Physical Chemistry, 2018Co-Authors: Piotr Pander, Agnieszka Swist, Roman Turczyn, Stephanie Pouget, David Djurado, Algirdas Lazauskas, Ramin Pashazadeh, Juozas V Grazulevicius, Radoslaw Motyka, Anastasia KlimashAbstract:Thianthrenes have been nearly forgotten as phosphors in recent years, but are now coming back, showing their strong potential in luminescent applications. Here, we present a comprehensive photophysical study of a carbazolyl derivative of Thianthrene in different matrices and environments. The diffusion of oxygen is slowed down in the rigid environment of Thianthrene organic crystals, suppressing their phosphorescence quenching.Triplet–triplet annihilation is also not significantly active in these systems. Both conditions facilitate the observation of simultaneous fluorescence and phosphorescence emissions at room temperature, in air, giving origin to strong white luminescence. Moreover, the color coordinates of the dual fluorescence–phosphorescence white emission, which is observed only in rigid amorphous media and in crystals, can be tuned.
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Observation of Dual Room Temperature Fluorescence–Phosphorescence in Air, in the Crystal Form of a Thianthrene Derivative
2018Co-Authors: Piotr Pander, Agnieszka Swist, Roman Turczyn, Stephanie Pouget, David Djurado, Algirdas Lazauskas, Ramin Pashazadeh, Juozas V Grazulevicius, Radoslaw Motyka, Anastasia KlimashAbstract:Thianthrenes have been nearly forgotten as phosphors in recent years, but are now coming back, showing their strong potential in luminescent applications. Here, we present a comprehensive photophysical study of a carbazolyl derivative of Thianthrene in different matrices and environments. The diffusion of oxygen is slowed down in the rigid environment of Thianthrene organic crystals, suppressing their phosphorescence quenching.Triplet–triplet annihilation is also not significantly active in these systems. Both conditions facilitate the observation of simultaneous fluorescence and phosphorescence emissions at room temperature, in air, giving origin to strong white luminescence. Moreover, the color coordinates of the dual fluorescence–phosphorescence white emission, which is observed only in rigid amorphous media and in crystals, can be tuned
Kenton H Whitmire - One of the best experts on this subject based on the ideXlab platform.
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adducts of Thianthrene and phenoxathiin cation radical tetrafluoroborates to 1 alkynes structures and formation of 1 5 thianthreniumyl and 1 10 phenoxathiiniumyl alkynes on alumina leading to α ketoylides and α ketols
Journal of Organic Chemistry, 2005Co-Authors: Paramashivappa Rangappa, Henry J Shine, John N Marx, Teyeb Ouldely, And Anna T Kelly, Kenton H WhitmireAbstract:[structure: see text] Thianthrene cation radical tetrafluoroborate (Th*+ BF4(-)) added to the terminal alkynes 1-pentyne, 1-hexyne, 1-heptyne, 1-octyne, 1-nonyne, and 1-decyne to form trans-1,2-bis(5-thianthreniumyl)alkene tetrafluoroborates (1-6). Similarly, addition of phenoxathiin cation radical tetrafluoroborate (PO*+ BF4(-)) to the same alkynes gave 1,2-bis(10-phenoxathiiniumyl)alkene tetrafluoroborates (7-12). The trans configuration of two of the adducts (1 and 4) was shown with X-ray crystallography. When solutions of 1-6 in chloroform were stirred with activated alumina, cis elimination of a proton and Thianthrene (Th) occurred with the formation of 1-(5-thianthreniumyl)alkyne tetrafluoroborates (1a-6a). Similar treatment of 8-12 caused elimination of a proton and phenoxathiin (PO) with formation of 1-(10-phenoxathiiniumyl)alkene tetrafluoroborates (8a-12a). Stirring of 1a-6a with alumina for short periods of time caused their conversion into 5-[(alpha-keto)alkyl]thianthrenium ylides (1b-6b) and alpha-ketols, RC(O)CH2OH (1c-6c).
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adducts of Thianthrene and phenoxathiin cation radical salts with symmetrical alkynes structure and formation of cumulenes on alumina leading to α diketones α hydroxyalkynes and α acetamidoalkynes
Journal of Organic Chemistry, 2005Co-Authors: Henry J Shine, Paramashivappa Rangappa, John N Marx, Dennis C Shelly, Teyeb Ouldely, Kenton H WhitmireAbstract:Thianthrene cation radical tetrafluoroborate (Th•+BF4-) added to 2-butyne, 3-hexyne, 4-octyne, and 5-decyne in MeCN to form trans bisadducts R(Th+)CC(Th+)R, where R = Me, Et, Pr, Bu (7a−d). Phenoxathiin cation radical tetrafluoroborate (PO•+BF4-) added similarly to the last three alkynes to form adducts R(PO+)CC(PO+)R, 8b−d. Cyclic monoadducts were not found. The trans structures of 7 and 8 were deduced with X-ray crystallography (7c) and NMR spectroscopy. When solutions of adducts in CHCl3 and MeCN were deposited on activated alumina, elimination of Thianthrene (Th) and phenoxathiin (PO) occurred almost quantitatively. Detailed studies with (7b−d) indicated that a cumulene (15) was formed by the elimination of Th and that 15 was subsequently converted into small amounts of other products. In CHCl3, these products were the respective alkyne, Thianthrene 5-oxide, an α-diketone (11), an α-hydroxyalkyne (12), and hydrogen. The same products were formed in MeCN along with an α-acetamidoalkyne (13). The format...
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decomposition of alkene adducts of Thianthrene cation radical in nitrile solvents formation of alkyl 2 oxazolines and a new class of four component products 5 1 alkoxyalkylidene ammonio alkylthianthrenium diperchlorates
Journal of Organic Chemistry, 2004Co-Authors: Henry J Shine, John N Marx, Teyeb Ouldely, Bing Jun Zhao, Kenton H WhitmireAbstract:The monoadducts (4a−d) of Thianthrene cation radical perchlorate (1a) and isobutene, 2-methylbutene, 2-methyl-2-butene, and 2-methylpentene decompose spontaneously in acetonitrile (MeCN) solution, with the formation of Thianthrene (Th). Decomposition of 4a (1,2-(5,10-thianthreniumdiyl)-2-methylpropane diperchlorate) and 4a‘, the corresponding dihexafluorophosphate, was studied in depth and extensively with 1H and 13C NMR spectroscopy. Decomposition of 4a was found to involve the solvent itself as well as water in the solvent, remaining from incomplete drying, and gave, apart from Th, successively, the perchlorate salts of 2,4,4-trimethyl-2-oxazoline (6) and 2-amino-2-methylpropyl acetate (7). These salts, 6-HClO4 and 7-HClO4, respectively, were prepared and used in understanding the reactions of 4a as well as the relationships among 6, 7, and 2-(acetylamino)-2-methyl propanol (8) in acidified MeCN solution. Decompositions of 4a−d in MeCN and other nitriles (RCN) containing an added alcohol (R‘OH) led to n...
Hiroyuki Morita - One of the best experts on this subject based on the ideXlab platform.
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synthesis of Thianthrene derivatives linked by carbon chains
Synthesis, 2013Co-Authors: Md Chanmiya Sheikh, Takasi Iwasawa, Akitaka Nakajima, Atsutaka Kitao, Noritatsu Tsubaki, Ryuta Miyatake, Toshiaki Yoshimura, Hiroyuki MoritaAbstract:Dithianthren-1-ylmethanol and 1,1′-methylenediThianthrene were prepared and their reactions were studied. Lithiation of 1,1′-methylenediThianthrene took place on the methylene carbon rather than on the Thianthrene framework, and when the lithiated derivative was allowed to react with thianthren-1-ylcarbaldehyde, sterically hindered 1,2,2-trithianthren-1-ylethanol was obtained in good yield. The structures of 1,1′-methylenediThianthrene and 1,2,2-trithianthren-1-ylethanol were confirmed by X-ray crystallography. To clarify the nature and reactivity of Thianthrene derivatives, we also prepared 1,6-(thianthren-1,9-diyl)hexane-1,6-diol (5,6,7,8,9,10-hexahydro-1,14-epithiodibenzo[b,j]thiacycloundecine-5,10-diol) as a model compound in which the 1- and 9-positions of Thianthrene are bridged by a carbon chain.
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synthesis of Thianthrene dimer by the coupling reaction of stannylThianthrenes in the presence of copper catalysts
Tetrahedron, 2011Co-Authors: Hiroyuki Morita, Md Chanmiya Sheikh, Yasutaka Oida, Takamine Ariga, Satoru Fukumoto, Takayoshi Fujii, Toshiaki YoshimuraAbstract:The coupling reaction of 1-tributylstannylThianthrene (5) and 2-tributylstannylThianthrene (7) in the presence of copper catalysts at rt afforded the Thianthrene dimer 1,1′-biThianthrene (3), 2,2′-biThianthrene (8), and 1,2′-diThianthrene (9) in high yields. Also we obtained Thianthrene oxide dimer (R,R) (S,S)-1-(10-S-monoxyThianthrene-1-yl)Thianthrene-10-S-monoxide (12) and (R,S) (S,R)-1-(10-S-monoxyThianthrene-1-yl)Thianthrene-10-S-monoxide (13) from 1-tributylstannyl-10-S-monoxyThianthrene (10) under the same reaction condition. The final structural conformation of 3, 8, 9, and 12 was performed by X-ray crystallographic analysis. Further, the solvent effects in the coupling reactions were also examined.
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photolytic aziridination by Thianthrene sulfilimine derivatives
Journal of Sulfur Chemistry, 2008Co-Authors: Tomoyuki Fujita, Atsushi Tatami, Wataru Kawashima, Daisuke Miyamoto, Mikako Yoshida, Naoko Tsuchiya, Hiroyuki Kawaguchi, Tetsuo Maeda, Hiroyuki MoritaAbstract:Photolyses of Thianthrene sulfilimine derivatives in the presence of several olefins were studied and found to afford the corresponding aziridines in good yields, particularly, in case of 2,8-dibromo-[5-(N-tosyl)imino]Thianthrene. This reaction was considered to proceed via generation of nitrene by photolytic S–N bond cleavage of Thianthrene sulfilimines. Further, photo-aziridination of olefins by Thianthrene sulfilimine derivatives was intensively studied to make clear the ability as nitrene precursors.
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photo sn bond cleavage and related reactions of Thianthrene sulfilimine derivatives
Tetrahedron, 2007Co-Authors: Tomoyuki Fujita, Atsushi Tatami, Wataru Kawashima, Yasushi Osawa, Hideo Kamiyama, Atsushi Nakanishi, Hiroyuki Kawaguchi, Tetsuo Maeda, Hiroyuki MoritaAbstract:Abstract Several 1- and 2-substituted Thianthrene sulfilimine derivatives were prepared and the selectivity toward oxidation and N-tosylimination under several conditions was studied. In the photolysis of trans-5-(N-p-tosyl)iminoThianthrene 10-oxide (trans-10), photo isomerization to cis-10 was observed. Further, photoimino-transfer reaction of sulfilimines and their 10-mono- and -dioxide derivatives to sulfides was intensively studied to make clear the ability as nitrene precursors.
