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..
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.
Sisler,Kotia
, p. 1700 (1971)
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.
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.
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.
Samarium diiodide-induced reduction of amorphous selenium: A facile synthesis of diaryl diselenides
Zhang,Jia,Zhou
, p. 1247 - 1252 (1994)
Samarium diiodide reduces amorphous selenium to Se2/2- in THF. Subsequent addition of aryldiazonium fluoborates affords diaryl diselenides in moderate to good yields.
Selenium halide-induced bridge formation in [2.2]paracyclophanes
Sarbu, Laura G.,Hopf, Henning,Jones, Peter G.,Birsa, Lucian M.
, p. 2550 - 2555 (2014)
An addition/elimination sequence of selenium halides to pseudo-geminally bis(acetylene) substituted [2.2]paracyclophanes leads to new bridges with an endo -exo-diene substructure. The reactions have been found to be sensitive to the substitution of the ethynyl group. The formation of dienes with a zig-zag configuration is related to that observed for non-conjugated cyclic diynes of medium ring size.
Metathesis of N-Silyl Compounds with Selenenyl Chlorides. First Preparation of a Selenenyl Azide and a Triselenenamide
Back, Thomas G.,Kerr, Russell G.
, p. 134 - 135 (1987)
The reaction of trimethylsilyl azide with mesityleneselenenyl chloride afforded mesityleneselenenyl azide, and tris(trimethylsilyl)amine reacted with benzeneselenenyl chloride to produce tribenzeneselenenamide.
A convenient new method for the preparation of diaryl diselenide
Liu,Chen
, p. 2673 - 2676 (1993)
Diaryliodonium salts react with sodium O, O-diethyl phosphoroselenoate in ethano-DMF at 70-80°C then hydrolyzed in basic medium and oxidized at room temperature to afford symmetric diaryl diselenides in better yields.
Catalyst-free gem-difunctionalization of fluoroalkyl-substituted diazo compound with diselenide or disulfide and NFSI
Li, Jiuling,Ma, Chaoqun,Xing, Dong,Hu, Wenhao
, p. 2101 - 2105 (2019)
The gem-difunctionalization of fluoroalkyl-substituted diazo compounds by utilizing diselenides or disulfides and NFSI under catalyst-free and mild conditions is reported. A series of gem-aminoselenolation and gem-aminosulfonylation products bearing fluoroalkyl substituents were obtained in high to excellent yields. Different types of conjugated diazo compounds are also applicable to this transformation. Preliminary mechanistic studies indicate that a selenoimidate intermediate generated from diselenide and NFSI is involved for this transformation.
The Anodic Acetoxylation of Alkylarylselenides
Jouikov, Viatcheslav,Ivkov, Valery,Fattahova, Dina
, p. 6045 - 6048 (1993)
Electrooxidation of alkylarylselenides in methanol in the presence of sodium acetate leads to the acetoxylation of the methylene group of selenides
Chalcogen-rich lanthanide clusters: Cluster reactivity and the influence of ancillary ligands on structure
Kornienko,Emge,Brennan
, p. 11933 - 11939 (2001)
Ytterbium metal reacts with PhEEPh (E = S, Se, Te) and elemental Se in pyridine to give (pyridine)8Yb4(SeSe)2(Se)2(μ 2-SPh)2(SPh)2, (py)8Yb4Se(SeSe)3(SeSeSePh)(Se 0.38SePh), and (py)8Yb4Se(SeSe)3-(SeSeTePh)(SeTePh), respectively. The SePh and TePh compounds contain a square array of Ln(III) ions all connected to a central Se2- ligand. Three edges of the square are bridged by diselenide ligands, with the fourth SeSe unit coordinating to an EPh ligand that has been displaced from an inner Yb coordination sphere. Differences in the two compounds have their origin in the relative strength of the Yb - E(Ph) bond. In the TePh compound, there is a complete insertion of Se into the remaining Yb - Te(Ph) bond to give a terminal SeTePh ligand, while in the SePh compound there is a compositional disorder in the structure comprised of a terminal SePh ligand and a minor component that has Se inserted into the Yb - Se(Ph) bond to give a terminal SeSePh ligand. The thiolate compound differs dramatically, crystallizing as a rhombohedral array of four Yb(III) ions connected by a pair of μ3-Se2- ligands, with the edges of the rhombus spanned by alternating diselenide and SPh. The SPh coordinate directly to Yb(III) ions in terminal or bridging modes. Cluster interconversion is facile: (py)4Yb(SePh)2 reduces (py)8Yb4Se(SeSe)3(SeSeSePh)(Se 0.38SePh) to give the cubane cluster [(py)2YbSe(SePh)]4, and the cubane reacts with elemental Se to give (py)8Yb4Se(SeSe)3(SeSeSePh)-(Se 0.38SePh). Upon thermolysis, these compounds give YbSex.
In situ synthesis of CuO nanoparticles over functionalized mesoporous silica and their application in catalytic syntheses of symmetrical diselenides
Das, Trisha,Chatterjee, Rana,Majee, Adinath,Uyama, Hiroshi,Morgan, David,Nandi, Mahasweta
, p. 17874 - 17886 (2019)
A versatile and novel catalyst, CuO nanoparticles immobilized over functionalized mesoporous silica (nCuO-FMS), has been synthesized over an organically modified mesoporous silica framework following a facile synthetic route. The surface of the silica support (SBA-15) is first grafted with the 3-aminopropyl silane group and then further functionalized with tris(4-formylphenyl)amine. The reaction is performed in such a way that a few -CHO groups remain free for further functionalization. Finally, the CuO nanoparticles immobilized on mesoporous silica are obtained by a one pot reaction between the functionalized silica, 2-aminophenol and CuCl2. The product obtained has been used as a catalyst for the syntheses of symmetrical diselenides in the presence of KOH as the base and dimethyl sulphoxide (DMSO) as the solvent. The materials have been characterized thoroughly by X-ray powder diffraction, nitrogen adsorption-desorption studies, transmission electron microscopy, thermal analysis and different spectroscopic techniques. The Cu content of the sample has been determined by atomic absorption spectrophotometry (AAS). The products of the catalytic studies have been identified and estimated by NMR spectroscopy. Almost 78% isolated yield could be achieved at 363 K within 3 hours of the reaction and the catalyst, nCuO-FMS, can be recycled at least up to five catalytic cycles.
Chemoselective reduction of organoselenocyanates to diselenides
Krief, Alain,Delmotte, Cathy,Dumont, Willy
, p. 3079 - 3080 (1997)
Selenocyanates possess an extremely high propensity to produce diselenides on reaction with selenols or selenolates. This is effectively observed when one molar equivalent of metal hydride or lithium triethyl borohydride or one fourth molar equivalent of metal borohydrides are reacted with organic selenocyanates.
Visible-light-induced oxidative coupling of vinylarenes with diselenides leading to α-aryl and α-alkyl selenomethyl ketones
Liu, Gong-Qing,Yi, Wei,Wang, Peng-Fei,Liu, Ji,Ma, Meng,Hao, Da-Yun,Ming, Liang,Ling, Yong
supporting information, p. 1840 - 1846 (2021/03/09)
A visible-light-induced oxidative coupling of diselenides with readily available vinylarenes is demonstrated. This benign protocol allows one to access a wide range of α-aryl and α-alkyl selenomethyl ketones in good yields with excellent functional group compatibility. The distinct advantages of this protocol over all previous methods include the use of a green solvent and air as an oxidant and the lack of a photocatalyst, a base, and an oxidant as well as better green chemistry matrices. Furthermore, the title reaction can be performed with natural sunlight, the most sustainable energy source imaginable. Additionally, the mild reaction conditions, easy operation and suitability for the modification of styrene-functionalized biomolecules make the current reaction system a more attractive method for the synthesis of a variety of medicinal and agrochemical compounds of interest.
Synthesis of Seleno Oxindoles via Electrochemical Cyclization of N-arylacrylamides with Diorganyl Diselenides
Wang, Xin-Yu,Zhong, Yuan-Fang,Mo, Zu-Yu,Wu, Shi-Hong,Xu, Yan-Li,Tang, Hai-Tao,Pan, Ying-Ming
supporting information, p. 208 - 214 (2020/12/04)
The tandem cyclization of acrylamide with diselenides facilitated by electrochemical oxidation was successfully developed. This strategy provided an environmentally friendly method for the construction of C?Se bond. A series of seleno oxindoles with pharmacological activity were obtained by using this well-designed tandem cyclization strategy. The in vitro antitumor activity of the compounds was also screened through MTT assay. Results showed that the seleno oxindoles exhibited better antitumor activity than other oxindole derivatives. (Figure presented.).
Visible Light-Induced Cascade Cyclization of 3-Aminoindazoles, Ynals, and Chalcogens: Access to Chalcogen-Containing Pyrimido[1,2- b]-indazoles
Zhou, Jinlei,Li, Wen,Zheng, Huitao,Pei, Yongyan,Liu, Xiang,Cao, Hua
supporting information, p. 2754 - 2759 (2021/04/12)
A direct cascade cyclization of 3-aminoindazoles, ynals, and accessible chalcogens facilitated by visible light has been developed. A series of fluoroactive selenium/tellurium-substituted pyrimido[1,2-b]-indazoles were easily accessed in moderate to good yields with a broad scope. Furthermore, we surveyed the spectral properties of selenide pyrimido[1,2-b]-indazoles prepared by this method.
