- Synthesis of Multivalent Organotellurium Chain-Transfer Agents by Post-modification and Their Applications in Living Radical Polymerization
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Functionalized or multivalent organotellurium chain-transfer agents (CTAs) for living radical polymerization were synthesized by post-modification, which involved the condensation between a carboxylic-acid-functionalized CTA and various amines in excellent yields without affecting the reactive tellurium moiety. The CTAs exhibited high synthetic versatility for radical polymerization and gave structurally well-controlled polymers, such as multiarmed polymers, from various monomers. Because all new CTAs are easily available on a large scale by simple purification, the current method significantly facilitates macromolecular engineering based on organotellurium-mediated radical polymerization (TERP).
- Fan, Weijia,Nakamura, Yasuyuki,Yamago, Shigeru
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- Homolytic reactions of diorganotellurium and diorganoditellurium compounds in solution; an EPR study
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The thermal and photochemical decompositions of dialkyltelluriums and dialkylditelluriums in t-butylbenzene solvent have been studied by EPR spectroscopy.On photolysis, di-t-butyl, diallyl, allyl methyl, and dibenzyl tellurium showed EPR spectra of t-butyl, allyl, allyl, and benzyl radicals respectively.Alkyl radicals were not detected directly on thermolysis in the range 300-370 K but, primary, secondary, and tertiary alkyl, benzyl and allyl telluriums gave spin adducts of the corresponding alkyl radical with nitrosodurene.Dimethyl tellurium was unreactive in the same temperature range.The rates of thermal decomposition of the diorgano telluriums at 315 K were found to be in the following order, as judged by the intensity of the spin adduct spectra: tBu2Te ca. tBuTeMe > (allyl)2Te ca. allylTeMe > sBu2Te > (benzyl)2Te > iPr2Te > Et2Te > Me2Te.For dihex-5-ethyltellurium the results were consistent with formation and cyclisation of hex-5-enyl and hex-5-enetelluryl radicals.In the case of dipent-4-enyltellurium, the results suggested that both exo- and endo-cyclisation of the pentene telluryl radicals were important.Di-isopropyl- and di-t-butyl-ditelluriums gave spin adducts of the corresponding alkyl radicals on therolysis in the same temperature range as the monoalkyltelluriums.
- Bell, William,Cole-Hamilton, David J.,Culshaw, Peter N.,McQueen, A. Ewan D.,Shenai-Khatkhate, D. V.,et al.
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- Synthesis of 1,2-ditellurane
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Freshly prepared solutions of disodium ditelluride react with diiodobutane to give small yields of 1,2-ditellurane.In contrast, reactions of α,α-bis(chloromethyl)-o-xylene and phthaloyl chloride give 3,4-benzo-1-telluracyclopentane and tellurophthalic anhydride respectively.
- Singh, Harkesh B.,Khanna, Pawan K.
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- Anion Recognition in Water by Charge-Neutral Halogen and Chalcogen Bonding Foldamer Receptors
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A novel strategy for the recognition of anions in water using charge-neutral σ-hole halogen and chalcogen bonding acyclic hosts is demonstrated for the first time. Exploiting the intrinsic hydrophobicity of halogen and chalcogen bond donor atoms integrated into a foldamer structural molecular framework containing hydrophilic functionalities, a series of water-soluble receptors was constructed for an anion recognition investigation. Isothermal titration calorimetry (ITC) binding studies with a range of anions revealed the receptors to display very strong and selective binding of large, weakly hydrated anions such as I- and ReO4-. This is achieved through the formation of 2:1 host-guest stoichiometric complex assemblies, resulting in an encapsulated anion stabilized by cooperative, multidentate, convergent σ-hole donors, as shown by molecular dynamics simulations carried out in water. Importantly, the combination of multiple σ-hole-anion interactions and hydrophobic collapse results in I- affinities in water that exceed all known σ-hole receptors, including cationic systems (β2 up to 1.68 × 1011 M-2). Furthermore, the anion binding affinities and selectivity trends of the first example of an all-chalcogen bonding anion receptor in pure water are compared with halogen bonding and hydrogen bonding receptor analogues. These results further advance and establish halogen and chalcogen bond donor functions as new tools for overcoming the challenging goal of anion recognition in pure water.
- Borissov, Arseni,Marques, Igor,Lim, Jason Y.C.,Félix, Vítor,Smith, Martin D.,Beer, Paul D.
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- THE PREPARATION OF DI-t-BUTYL DITELLURIDE AND DI-t-BUTYL TELLURIDE AND THE 125Te NMR AND MOESSBAUER SPECTRA OF SOME DIALKYL TELLURIDES AND DITELLURIDES
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The synthesis of di-t-butyl ditelluride, t-Bu2Te2, an di-t-butyl telluride, t-Bu2Te, are reported together with that of di-(neo-hexyl) ditelluride.New syntheses of Me2Te2 and i-Pr2Te2 are presented.The high resolution 125Te NMR data and the Moessbauer data for these compounds are discussed.The use of tellurium-proton couplings in high resolution 125Te NMR spectra in assigning the resonances in mixed dialkyl ditellurides is also illustrated.
- Jones, C.H.W.,Sharma, R.D.
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- Polyynes to Polycycles: Domino Reactions Forming Polyfused Chalcogenophenes
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Polyfused chalcogenophenes are prepared in one step through polyelectrophilic cyclization of polyynes using the ambiphilic reagent MeACl (A = S, Se, or Te). Up to four new rings have been generated under mild conditions, including thiophenes, selenophenes, and tellurophenes.
- Dillon, Annaliese S.,Flynn, Bernard L.
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supporting information
p. 2987 - 2990
(2020/04/09)
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- RADICAL POLYMERIZATION INITIATOR AND METHOD FOR PRODUCING POLYMERS
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The present invention involves a radical polymerization initiator comprising an organotellurium compound represented by a formula (1), wherein R1 represents an alkyl group or the like, each of R2 and R3 independently represents a hydrogen atom or the like, and each of R4, R5, and R6 independently represents a hydrogen atom or the like. The present invention provides: a radical polymerization initiator that is useful for producing a polymer that includes a double bond at the molecular terminal; and a method for producing a polymer that utilizes the radical polymerization initiator.
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Paragraph 0139-0142
(2016/10/31)
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- Reaction of 1,1-dichloroethane with tellurium in the system hydrazine hydrate-potassium hydroxide
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The reaction of 1,1-dichloroethane with tellurium in the system hydrazine hydrate-potassium hydroxide gave ethyltellanyl derivatives as a result of replacement of one chlorine atom in the substrate by tellurium, and of the other, by hydrogen. Probable mechanisms of reduction of the C-Cl bond and mass spectra of the products were considered. The mass spectra of ditelluroacetals revealed unusual rearrangement of the molecular ion, leading to the formation of Te-Te and new C-C bond.
- Levanova,Grabel'nykh,Kolesnikov,Klyba,Zhanchipova,Albanov,Russavskaya,Korchevin
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experimental part
p. 988 - 992
(2011/02/26)
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- Reaction of tellurium with dichloromethane in the system hydrazine hydrate-alkali
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Tellurium reacts with dichloromethane in the system hydrazine hydrate-alkali substituting one chlorine atom by tellurium whereas the second chlorine atom undergoes reductive substitution by hydrogen leading to the formation of methyltellanyl derivatives.
- Levanova,Grabel'Nykh,Russavskaya,Klyba,Albanov,Korchevin
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experimental part
p. 2321 - 2327
(2010/05/15)
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- Reactions of dichloromethane with chalcogens and dimethyl chalcogenides in the hydrazine hydrate-alkali system
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Methods of synthesis of compounds MeY(CH2Y) n Me (Y=S, Se, Te; n = 1-3) containing several identical or different chalcogen atoms are suggested. The methods are based on the reactions of dichloromethane with elemental chalcogens (Ys
- Levanova,Vshivtsev,Sukhomazova,Grabel'nykh,Russavskaya,Zhanchipova,Klyba,Albanov,Korchevin
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experimental part
p. 1734 - 1741
(2009/02/07)
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- ORGANIC ANTIMONY COMPOUND, PROCESS FOR PRODUCING THE SAME, LIVING RADICAL POLYMERIZATION INITIATOR, PROCESS FOR PRODUCING POLYMER USING THE SAME, AND POLYMER
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1. An organoantimony compound represented by the formula (1), processes for producing polymers with use of the compound, and polymers wherein R 1 and R 2 are C 1 -C 8 alkyl, aryl, substituted aryl or an aromatic heterocyclic group, R 3 and R 4 are each a hydrogen atom or C 1 -C 8 alkyl, and R 5 is aryl, substituted aryl, an aromatic heterocyclic group, oxycarbonyl or cyano. P
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Page/Page column 37
(2008/06/13)
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- ORGANIC BISMUTH COMPOUND, METHOD FOR PRODUCING SAME, LIVING RADICAL POLYMERIZATION INITIATOR, METHOD FOR PRODUCING POLYMER USING SAME, AND POLYMER
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An organobismuth compound represented by the formula (1) wherein R1 and R2 are C1-C8 alkyl, aryl, substituted aryl or an aromatic heterocyclic group, R3 and R4 are each a hydrogen atom or C1-C8 alkyl, and R5 is aryl, substituted aryl, an aromatic heterocyclic group, acyl, amido, oxycarbonyl or cyano.
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Page/Page column 16
(2010/11/28)
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- Synthesis of 1,3-bis(organylchalcogeno)propanes and 1,2-dichalcogenolanes having different chalcogen atoms in the molecule
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Oligomeric trimethylene dichalcogenides and the corresponding 1,2-dichalcogenolanes having both similar and different chalcogen atoms in the molecule were synthesized by reactions of 1-bromo-3-chloropropanes with two elemental chalcogens (S, Se; S, Te; Se, Te) activated by the system hydrazine hydrate-alkali. Reductive cleavage of the oligomeric products in the system hydrazine hydrate-alkali, followed by alkylation with methyl iodide or ethyl bromide gave 1,3-bis(alkylchalcogeno)propanes. The latter were also obtained from the corresponding dialkyl dichalcogenides and 1-bromo-3-chloropropane in the alkaline reducing system.
- Elaev,Grabel'nykh,Russavskaya,Klyba,Zhanchipova,Levanova,Sukhomazova,Albanov,Mamaseva,Korchevin
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- Reaction of 1-bromo-3-chloropropane with tellur and dimethyltelluride in the system of hydrazine hydrate-alkali
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A synthesis of oligomeric substance of thiocol type, the poly(trimethyleneditelluride), from 1-bromo-3-chloropropane and elemental tellurium is performed using a hydrazine hydrate-alkali system. Reductive splitting of the tellurocol followed by alkylation with methyl iodide give rise to preparation of bis(methyltelluro)propane, which was synthesized also from dimethyltelluride and 1,3-dihalopropanes using the N2H 4?H2O/KOH system. Mass spectra of the synthesized low molecular weight organotellurium compounds are considered. Pleiades Publishing, Inc., 2006.
- Russavskaya,Levanova,Sukhomazova,Grabelnykh,Elaev,Klyba,Zhanchipova,Albanov,Korotaeva,Totyashinova,Korchevin
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p. 726 - 729
(2008/02/02)
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- Synthesis of cyclic halooxatelluranes via dehalogenation of α-halo carbonyl compounds with tellurides containing hydroxy group on side chain
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The synthesis of cyclic halooxatelluranes (3a, 4a-d, 5a) has been achieved via dehalogenation of α-halo carbonyl compounds (2A-F) with tellurides(1a-d) containing hydroxy group on the side chain. Halophilicity of the tellurides was compared with that of selenides and a plausible reaction mechanism is discussed.
- Zhang, Jian,Saito, Shinichi,Takahashi, Tamiko,Koizumi, Toru
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p. 575 - 584
(2007/10/03)
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- NEW ROUTE TO ORGANIC SELENIDES AND TELLURIDES
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A new simple and convenient synthetic route to organic chalcogenides R2Y (R = alkyl, allyl, benzyl; Y = Se, Te) is developed, which involves generation of Se2- and Te2- anions from Se and Te in the system KOH-hydrazine hydrate, where the latter plays the role of both the medium and reducing agent.Subsequent alkylation of the anions with the corresponding alkyl halides furnishes the target chalcogenides in almost 95percent yield.Alkyl chlorides react faster than alkyl bromides and alkyl iodides.
- Korchevin, N. A.,Podkuiko, P. A.,Stankevich, V. K.,Deryagina, E. N.,Trofimov, B. A.
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- Preparation of dialkyl tellurium and dialkyl selenium
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Dialkyl SE and TE compounds are prepared by reacting a Na chalcogenide with a alkyl halide in a two-phase system of solvents.
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- (1)H and (13)C NMR Studies on the Positional Isomers of Methyl Selenalaurate and Telluralaurate
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A report is given of the (1)H and (13)C NMR spectra of a series of methyl selenalaurates and telluralaurates in which successive methylene groups have been replaced by a selenium or a tellurium atom.The effect on contiguous carbons is a marked upfield shift (shielding) while the protons attached to these carbons are deshielded.The β-and γ protons are weakly deshielded.
- Lie Ken Jie, Marcel S. F.,Yan-Kit, Cheung,Chau, Sherman H.,Yan, Bonnie F. Y.
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p. 501 - 508
(2007/10/02)
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- LITHIUM ORGANYL-POLYCHALCOGENOLATES
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Lithium organyl-selenolates, RSeLi or tellurolates, RTeLi insert further equivalents of chalcogens with formation of selenyl-selenolates, RSeSeLi or tellurenyl-tellurolates, RTeTeLi (R=Me, n-Bu, s-Bu, t-Bu, Ph).Mixed anions are only formed if the chalcogen insertion order corresponds with an increase of electronegativity, i.e.: RTeSeLi, RTeSLi, RSeSLi and n-BuTeSeSLi.All species have been characterized by 77-Se and 125-Te NMR-spectroscopy.Tellurenyl-tellurolates and tellurenyl-selenolates are stable at room temperature, selenyl-selenolates and chalcogenyl-thiolatesdisproportionate.The chemical integrity of the chalcogenyl-chalcogenolates was checked by methylation with methyl triflate.The formed organyl-methyl-dichalcogenides exhibit symmetrization equilibria that are also obtained by mixing the symmetric conpounds.Oxidation of tellurenyl-selenolates affords di(organyl-tellurenyl) selenides, (RTe)2Se (R=Me, n-Bu, t-Bu, Ph, p-MeC6H4, 2-thienyl) and (RTe)2Se2 for R=(Me3Si)3C.In solution (RTe)2Se are in equilibrium with R2Te2 and (RTe)2Se2.
- Koellemann, Christoph,Obendorf, Dagmar,Sladky, Fritz
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- Synthesis of chelating ditelluroether ligands, RTeCH2CH2CH2TeR (R = Me, Ph)
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RTeLi (R = Me, Ph), prepared in situ in tetrahydrofuran from RLi and Te, react at low temperatures with 1,3-dihalopropanes, X(CH2)3X (X = Cl, Br), to give high yields of RTe(CH2)3TeR. At ambient or higher temperatures these reactions yield mainly R2Te2. The RTeCH2TeR are made analogously, but 1,2-dichloroethane gave only R2Te2.
- Hope, Eric G.,Kemmitt, Tim,Levason, William
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p. 206 - 207
(2008/10/08)
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- A Novel Synthesis of Organic Tellurium Compounds by the Use of Electrochemically Generated Polytelluride-ions
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The cathodic polarisation of a tellurium electrode in aprotic solutions gives rise to polytelluride anions, which react with alkylhalides to the corresponding disubstituted ditellurides.By this method of electrosynthesis a number of organic ditellurides can be simply prepared and whithout danger.Dialkylditellurides of the general formula R-Te-Te-R (2a-r) can be produced with high yields.The reaction with α,ω-dihalides gives heterocycles, which involve one or two tellurium atoms in the ring (5a-d, 6-8).The electrochemical reduction of tellurium in the presence of methyliodid yields trimethyltelluroniumiodid (9).
- Merkel, G.,Berge, H.,Jeroschewski, P.
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p. 467 - 478
(2007/10/02)
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- 123m Te-Labeled biochemicals and method of preparation
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A novel class of 123m Te-labeled steroids and amino acids is provided by the method of reacting a 123m Te symmetric diorgano ditelluride with a hydride reducing agent and a source of alkali metal ions to form an alkali metal organo telluride. The alkali metal organo telluride is reacted with a primary halogenated steroidal side chain, amino acid, or amino acid precursor such as hydantoin. The novel compounds are useful as biological tracers and as organal imaging agents.
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