- Arylation of n-hexylthiol and n-hexyl phenyl sulfide using diphenyliodonium triflate: Synthetic and mechanistic aspects - Application to the transformation of n-hexylthiol to n-hexylselenide
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n-Hexyl diphenylsulfonium triflate has been efficiently prepared from n-hexylthiol and diphenyliodonium triflate and has been efficiently transformed to n-hexyl selenide. Georg Thieme Verlag Stuttgart.
- Krief, Alain,Dumont, Willy,Robert, Michael
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- A fast and direct iodide-catalyzed oxidative 2-selenylation of tryptophan
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A metal-free 2-selenylation of tryptophan derivatives is reported, where the use of iodide as the catalyst and oxone as the oxidant is key to obtain high yields. Various functional groups within the di-seleny and the indole ring are tolerated, and no racemization is generally observed.
- Gao, Yu-Ting,Liu, Shao-Dong,Cheng, Liang,Liu, Li
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supporting information
p. 3504 - 3507
(2021/04/12)
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- Selenium-containing compound and preparation and application thereof
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The invention discloses a compound shown as a formula (I), or a pharmaceutically acceptable salt, enantiomer, diastereoisomer, raceme, solvate, hydrate, polymorph, prodrug or isotope variant thereof,a mixture of the substances, and a novel selenium-contai
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Paragraph 0343-0348
(2021/03/30)
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- An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction
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Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.
- Lim, Yoo Jin,Shin, Na Hye,Kim, Chorong,Kim, Ye Eun,Cho, Hyunsung,Park, Myung-Sook,Lee, Sang Hyup
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- A Scalable Process for the Synthesis of 1,2-Dialkyldiselanes and 1-Alkaneselenols
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A four-step telescoped process for the synthesis of 1-alkaneselenols entails (1) the rapid formation of potassium selenocyanate from potassium cyanide and selenium in methanol, (2) the nucleophilic substitution of bromoalkanes or alkyl tosylates with potassium selenocyanate, (3) the mild base-catalyzed conversion of the resultant 1-alkaneselenocyanates to 1,2-dialkyldiselanes (the Krief reaction), and (4) the reduction of the resultant 1,2-dialkyldiselanes with hypophosphorous acid to give the desired 1-alkaneselenols. The process has been used to produce 1-octaneselenol on a 10.4 mol scale. Nine examples of the process are described.
- Cooksey, John P.,Kocieński, Philip J.,Blacker, A. John
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supporting information
p. 2571 - 2575
(2019/11/14)
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- Sterically encumbered hexakis(alkylseleno)benzenes: conformational behavior of hexakis(iso-propylselenomethyl)benzene toward Hg2+ ions on selective recognition
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An efficient synthesis and structural aspects of a novel class of hexakis(alkylseleno)benzenes [(RSeCH2)6C6] (R = Me, iPr, nBu, sBu, tBu, nPn, nHx, nOct, 1-methylnaphthalene) by the reaction of hexakis(bromomethyl)benzene with RSe- ions is demonstrated. Preliminary data on ion-sensing properties reveal that these species may act as selective ionophores for Hg2+ ions.
- Singh, Jai Deo,Maheshwari, Monika,Khan, Shabana,Butcher, Raymond J.
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p. 117 - 121
(2008/04/13)
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- Synthesis of primary-alkyl selenols and selenides from primary-alkyl thiols involving diphenyl sulfonium salts
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Hexyl thiol has been transformed to hexyl selenol and related selenides and selenocyanate by substitution of the corresponding hexyldiphenylsulfonium tetrafluoroborate with selenium nucleophiles. The Royal Society of Chemistry 2005.
- Krief, Alain,Dumont, Willy,Robert, Michael
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p. 2167 - 2168
(2007/10/03)
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- A preparation of alkyl or alkenyl N,N-dimethylchalcogenocarbamates and their one-step conversion into symmetrical dialkyl or dialkenyl dichalcogenides
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Alkyl or alkenyl N,N-dimethylchalcogenocarbamates were easily prepared by a stepwise treatment of bis(N,N-dimethylcarbamoyl) dichalcogenides with NaH or NaBH4, followed by various alkylating agents or acetylenes bearing electron-withdrawing sub
- Shimada, Kazuaki,Oikawa, Seiji,Nakamura, Hidenori,Moro-Oka, Akiko,Kikuchi, Miho,Maruyama, Akiko,Suzuki, Takahiro,Kogawa, Hisashi,Inoue, Yukiko,Gong, Yaling,Aoyagi, Shigenobu,Takikawa, Yuji
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p. 899 - 905
(2007/10/03)
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- Conditions-driven selective synthesis of selenides and selenols from elemental selenium
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Sodium borohydride in DMF is able to reduce elemental selenium in the presence of ethanol. Alkylation of the species resulting from the reaction of 2:1 molar equivalents of NaBH4/Se allows the selective synthesis, under very mild conditions, of symmetrical dialkyl selenides. Addition of formic acid, prior to that of the electrophile, permits the synthesis of the corresponding selenols.
- Krief, Alain,Trabelsi, Mahmoud,Dumont, Willy,Derock, Michel
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p. 1751 - 1754
(2007/10/03)
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- Synthesis of diselenides and selenides from elemental selenium
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Sodium hydride is able to reduce elemental selenium to sodium diselenide (Na2Se2), but not to sodium selenide (Na2Se). Dialkyl diselenides and even dialkyl selenides, including unsymmetrical dialkyl selenides, can be nevertheless synthesized using the proper Se/NaH ratio (1/1 or 1/2).
- Krief, Alain,Derock, Michel
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p. 3083 - 3086
(2007/10/03)
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- Preparation of diselenides by the oxidation of selenols using trichloroisocyanuric acid
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Selenols are readily oxidized to diselenides by a solution of pyridine, water, benzoic acid, and trichloroisocyanuric acid in acetonitrile and methylene chloride.
- Zhong,Guo
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p. 1507 - 1510
(2007/10/03)
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- A synthetic method for diselenides under phase-transfer conditions
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Diselenides were easily prepared in high yields by the alkylation of sodium diselenide on halides in water under phase-transfer conditions.
- Hu, Xubo,Tian, Zhenjiao,Lu, Xueran,Chen, Yuanyin
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p. 553 - 557
(2007/10/03)
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- First example of selenium transfer reaction of primary selenoamides and selenourea. Novel synthesis of dialkyl diselenides from alkyl halides
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As selenium transfer reagents, arylselenoamides react with a variety of alkyl halides in ethanol under mild conditions to give dialkyl diselenides in excellent yields.Similarly, alkyl halides treated with selenourea form dialkyl diselenides.The possible mechanism is discussed. Keywords: Selenium; Selenoamides; Diselenides; Selenourea; Alkyl halide
- Ming-De, Ruan,Hua-Rong, Zhao,Wei-Qiang, Fan,Xun-Jun, Zhou
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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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- Synthesis Utilizing Reducing Ability of Carbon Monoxide: A New Method for Selective Synthesis of Diorganyl Selenides and Diselenides Using a Selenium-Carbon Monoxide-Water Reaction System
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A new approach to the synthesis of diorganyl selenides and diselenides is described.Selective generation of tertiary amine salts of hydrogen selenide (->*+>) and hydrogen diselenide (->*+>) ha
- Nishiyama, Yutaka,Katsuura, Akio,Negoro, Atsuhito,Hamanaka, Sawako,Miyoshi, Noritaka,et al.
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p. 3776 - 3780
(2007/10/02)
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- A convenient method for the preparation of dialkylditellurides and dialkyldiselenides
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Dialkylditellurides 3 and dialkyldiselenides 4 were prepared in high yields and in a one-pot procedure by the reduction of elemental tellurium and selenium with phenyl hydrazine in basic medium (NaOH/DMF) followed by treatment with organohalides.
- Li,Bao,Lue,Zhou
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p. 799 - 806
(2007/10/02)
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- Pharmaceutical compositions having antineoplastic activity
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Compositions containing as antineoplastic active principloe only dialkyl diselenides show a very promising activity not withstanding a remarkably lower toxicity in comparison with that of known combinations of the same dialkyldi selenides with other active principles.
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- Fluorodestannylation. A Powerful Technique to Liberate Anions of Oxygen, Sulfur, Selenium, and Carbon
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Fluoride ions smoothly destannylate organotin chalcogenides to liberate nucleophilic chalcogenide ions; hence the first nucleophilic oxide (O2-) and selenide (Se2-) transfer agents are reported where the tin atom serves as "group 16 (VIB) transfer agent".In the presence of crown ethers or ammonium salts, this process results in a new way to generate "naked" nucleophiles.Ethers and selenides are formed in good to excellent yield.In addition, a useful C-C bond-forming reaction has been developed by using alkyltins with aldehydes and acid chlorides in the presence of fluroide ion.Aspects concerning reactivity and mechanism are presented.Finally, the generality of the fluorodestannylation procedure and the differences with parallel silicon chemistry are detailed.
- Harpp, David N.,Gingras, Marc
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p. 7737 - 7745
(2007/10/02)
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- Flash Pyrolysis of Selenides. Syntheses of Bibenzyls, Olefins, and Related Compounds
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Pyrolyses of a series of selenides and diselenides were studied. Selenides and diselenides bound with an active methylene group like benzyl gave a variety of substituted bibenzyls and related ethane derivatives in high yields. Other diselenides were easily caused to cleave to give various aromatic and aliphatic olefins in good yields together with elemental selenium. Lepidopterene, paracyclophane, and benzocyclobutene were prepared by thermal cleavage of their corresponding phenylselenomethyl-substituted compounds as an application of the pyrolysis concerned.
- Higuchi, Hiroyuki,Otsubo, Tetsuo,Ogura, Fumio,Yamaguchi, Hachiro,Sakata, Yoshiteru,Misumi, Soichi
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p. 182 - 187
(2007/10/02)
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- Selenocyanation using a combined reagent of triphenylphosphine and selenocyanogen. A new and simple synthesis of alkyl selenocyanates and symmetrical alkyl diselenides from alcohols
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A novel reagent Ph3SeCN)2, easily prepared by adding an equimolar amount of tri-phenylphosphine to selenocyanogen solution in methylene chloride and tetrahydrofuran reacts below -60° with primary alcohols to produce directly the corr
- Tamura,Adachi,Kawasaki,Kita
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p. 2251 - 2252
(2007/10/12)
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