1666-13-3Relevant articles and documents
Kinetic Study for Reactions of Phenylseleno Radical with Vinyl Monomers
Ito, Osamu
, p. 850 - 853 (1983)
The reactivities of the phenylseleno radical (PheSe.) generated by flash photolysis of diphenyl diselenide have been determined.Low reactivities of PhSe. toward oxygen, hydrogen -atom donors, and halogen-atom donors have been confirmed.With vinyl monomers (CH2=CHY) PhSe. reacts in a reversible fashion; by the addition of oxygen as a selective radical trap to the adduct radicals (PhSeCH2C.HY), the absolute addition rate constants have been determined.The reverse rate constants and the equilibrium constants have been estimated as relative ones from which the thermodynamic stabilities of the adduct radicals have been elucidated.The addition rates increase mainly with the stabilities of the adduct radicals and subsequently with the polar nature of the transition state.The lower reactivity of PhSe. compared with the phenylthio radical (PhS.) is attributed to the greater stabilization of an unpaired electron in PhSe. than that in PhS..
Trifluoromethylthiolative 1,2-difunctionalization of alkenes with diselenides and AgSCF3
Saravanan, Perumal,Anbarasan, Pazhamalai
, p. 4639 - 4642 (2019)
An efficient regioselective difunctionalization of alkenes via trifluoromethylthiolation has been accomplished employing diaryl diselenide and AgSCF3 in the presence of BF3·OEt2. Various substituted 1,2-dichalcogenated products having the SCF3 moiety were synthesized in good to excellent yields under mild conditions. The preliminary mechanistic investigation revealed the possible reaction pathway and unique combination of diselenide and AgSCF3 for successful transformation.
Laser-flash photolysis of naphthyl diselenides; Reactivities of naphthylseleno radicals
Alam,Ito,Koga,Quchi
, p. 193 - 200 (1998)
Transient absorption spectra of 1-naphthylseleno (1-NaphSe·), and 2-naphthylseleno (2-NaphSe·) radicals, which are generated by laser-flash photolysis of the corresponding diselenides, were observed. The reactions of 1-NaphSe·, and 2-NaphSe· with 2-methyl-1,3-butadiene and α-methylstyrene were investigated by following the decay rates of these seleno radicals. By both steady-state and laser-flash photolysis, it is proved that these seleno radicals add to alkenes in a reversible manner. The reaction rate constants for such reversible addition reactions were determined by conducting the reaction in the presence of O2, which traps selectively the carbon-centered radicals formed by the addition reaction of the seleno radicals to the alkenes. The reactivity of 2-NaphSe· is higher than that of 1-NaphSe·, both of which are less reactive than PhSe·. These reactivities were interpreted with the properties of SOMO calculated by MO method.
Efficient Syntheses of Diselenides from Selenols
Krief, A.,Mahieu, A. F. De,Dumont, W.,Trabelsi, M.
, p. 131 - 133 (1988)
Diselenides are quite instantaneously and quantitatively prepared by oxidation of selenols with 30 percent aqueous hydrogen peroxide or with the corresponding seleninic acids.
Stereoselective synthesis of (E)-vinylic selenides by palladium catalyzed cross-coupling reactions
Huang, Xian,Zhu, Liu-Sheng
, p. 9 - 11 (1996)
Hydrozirconation of arylselenoethynes gives zirconium (IV) complexes 3, which are cross-coupled with aryl halides in the presence of tetrakis (triphenylphosphine) palladium catalyst to afford (E)-vinylic selenides 5 in high yield.
A CONVENIENT SYNTHESIS OF PHENYL SELENOCYANATE
Tomoda, Shuji,Takeuchi, Yoshito,Nomura, Yujiro
, p. 1069 - 1070 (1981)
Treatment of benzeneselenenyl chloride with trimethylsilyl cyanide in various organic solvents provided phenyl selenocyanate in virtually quantitative yield.The reaction presents a very simple preparation of the useful selenenylation agent.
One-pot synthesis of 1-(E)-phenylethenyl-1,2,3-triazoles by sequential click-elimination reaction from 2-azido-1-phenyl-1-(Phenylseleno)ethane
Su, Hai-You,Sheng, Shou-Ri,Zhang, Xiao-Lan,Ding, Xiao-Ying,Cai, Ming-Zhong
, p. 1591 - 1598 (2013)
A new convenient one-pot, two-step procedure involving sequential click chemistry and oxidation-elimination reaction for the preparation of 1,4-disubstituted 1,2,3-triazoles bearing 1-(E)-phenylethenyl group from 2-azido-1-phenyl-1-(phenylseleno)ethane is described. The prominent features of this protocol are mild reaction conditions, operational simplicity, and good to high yields of products, as well as avoidance of the isolation of the selenated intermediate. Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental files: Additional figures.
CuO nanoparticles-catalyzed a novel method to the synthesis of symmetrical diselenides from aryl halides: selenoamide as an organic Se-donor reagent
Soleiman-Beigi, Mohammad,Yavari, Issa,Sadeghizadeh, Fatemeh
, p. 2239 - 2246 (2018)
A new method is reported for the synthesis of symmetrical diaryldiselenides from aryl halides using selenoamide as an organic Se-donor reagent in the presence of copper (II) oxide nanoparticles. CuO nanoparticles were found to be an efficient and inexpensive catalyst for ligand-free C-Se bond formation with a series of symmetrical diaryldiselenides obtained in good to excellent yield.
Allylic and Propargylic Phenyl Selenide Oxygenation by Cyclohexanone Oxygenase: -Sigmatropic Rearrangement of the Enzyme-generated Selenoxide
Latham, John A.,Branchaud, Bruce P.,Chen, Y.-C. Jack,Walsh, Christopher
, p. 528 - 530 (1986)
Enzymic oxidation of propargylic and allylic selenides has been carried out and the resulting selenoxides found to readily undergo 2,3-sigmatropic rearrangement; the propargylic product undergoes fragmentation while the allylic product yields racemic alcohols.
Chemoselective reduction of organoselenocyanates to diselenides and selenolates
Krief, Alain,Delmotte, Cathy,Dumont, Willy
, p. 12147 - 12158 (1997)
Selenocyanates produce selenolates or diselenides on reaction with metal hydrides (NaH, LiHBEt3, LiBH4, NaBH4). The former transformation is performed with 2 molar equivalents of sodium hydride or lithium triethyl borohydride or 1.25 molar equivalent of metal borohydrides. The second one is performed with lower amount of reducing agent (1 molar equivalent of sodium hydride or lithium triethyl borohydride or 0.25 equivalent of metal borohydrides). Intermediate formation of a selenol or a selenolate which reacts on the unreacted selenocyanate is suspected in the later transformation.
