1482-82-2Relevant articles and documents
Reactions of selenobenzamide and alkyl halides. Synthesis of dialkyl selenides and diselenides
Zhang, Xiao-Bo,Ruan, Ming-De,Fan, Wei-Qiang
, p. 4665 - 4670 (1996)
In the absence of base, the reaction of selenobenzamide with alkyl halides gives the dialkyl diselenides as the major product. While the reaction of selenobenzamide and an alkyl halide is carried out in a 1:2 molar ratio and in the presence of strong base, the dialkyl selenides predominate.
Chemoselective synthesis of fuctionalized diselenides
Salama,Bernard
, p. 5711 - 5714 (1995)
The action of LiEt3BH or DIBAL-H on various functionalized selenocyanates was proven to be an efficient means to establish chemoselectively the diselenide bond, under very mild conditions. The mechanism was shown to involve a selenophilic hydri
A convenient one-pot synthesis of dibenzyl diselenides under microwave irradiation conditions
Wang, Jin-Xian,Bai, Lin,Li, Wenbo,Hu, Yulai
, p. 325 - 332 (2000)
A simple, rapid and efficient method for the synthesis of dibenzyl diselenides under microwave irradiation is reported. The effect of microwave irradiation power, times and solvent on the reaction is investigated.
An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction
Lim, Yoo Jin,Shin, Na Hye,Kim, Chorong,Kim, Ye Eun,Cho, Hyunsung,Park, Myung-Sook,Lee, Sang Hyup
, (2020)
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.
A synthetic method for diselenides under phase-transfer conditions
Hu, Xubo,Tian, Zhenjiao,Lu, Xueran,Chen, Yuanyin
, p. 553 - 557 (1997)
Diselenides were easily prepared in high yields by the alkylation of sodium diselenide on halides in water under phase-transfer conditions.
Selenocyanation using a combined reagent of triphenylphosphine and selenocyanogen. A new and simple synthesis of alkyl selenocyanates and symmetrical alkyl diselenides from alcohols
Tamura,Adachi,Kawasaki,Kita
, p. 2251 - 2252 (1979)
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
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Lewicki,J.W. et al.
, p. 552 (1976)
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Chu et al.
, p. 4905 (1975)
The Convenient Syntheses of Organoselenium Reagents
Syper, Ludwig,Mlochowski, Jacek
, p. 439 - 442 (1984)
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Hydrolysis-Based Small-Molecule Hydrogen Selenide (H2Se) Donors for Intracellular H2Se Delivery
Bolton, Sarah G.,Chouinard, Julie E.,Garcia, Arman C.,Golledge, Stephen L.,Newton, Turner D.,Pluth, Michael D.,Zakharov, Lev N.
, p. 19542 - 19550 (2021/11/23)
Hydrogen selenide (H2Se) is a central metabolite in the biological processing of selenium for incorporation into selenoproteins, which play crucial antioxidant roles in biological systems. Despite being integral to proper physiological function, this reactive selenium species (RSeS) has received limited attention. We recently reported an early example of a H2Se donor (TDN1042) that exhibited slow, sustained release through hydrolysis. Here we expand that technology based on the P-Se motif to develop cyclic-PSe compounds with increased rates of hydrolysis and function through well-defined mechanisms as monitored by 31P and 77Se NMR spectroscopy. In addition, we report a colorimetric method based on the reaction of H2Se with NBD-Cl to generate NBD-SeH (λmax = 551 nm), which can be used to detect free H2Se. Furthermore, we use TOF-SIMS (time of flight secondary ion mass spectroscopy) to demonstrate that these H2Se donors are cell permeable and use this technique for spatial mapping of the intracellular Se content after H2Se delivery. Moreover, these H2Se donors reduce endogenous intracellular reactive oxygen species (ROS) levels. Taken together, this work expands the toolbox of H2Se donor technology and sets the stage for future work focused on the biological activity and beneficial applications of H2Se and related bioinorganic RSeS.
Metal-free synthesis of unsymmetrical selenides from pyridinium salts and diselenides catalysed by visible light
Ji, Liangshuo,Qiao, Jiamin,Li, Ankun,Jiang, Zeyi,Lu, Kui,Zhao, Xia
supporting information, (2021/05/04)
We report the first metal-free selenolations of pyridinium salts with diselenides to prepare unsymmetrical organoselenides catalysed by visible light. This protocol is an efficient and green method for the preparation of unsymmetrical organoselenides because metal-free conditions and readily accessible diselenides are used.
Synthesis of unsymmetrical glycosyl diselenides by the treatment of symmetrical diselenides with glycosyl selenocyanates
Manna, Tapasi,Misra, Anup Kumar,Rana, Abhijit
, (2021/08/03)
A novel reaction condition has been developed for the synthesis of unsymmetrical glycosyl diselenide derivatives in excellent yield by the reaction of glycosyl selenocyanates as selenol surrogates with symmetrical diselenides in the presence of hydrazine monohydrate at room temperature. The reaction metal-free condition is reasonably fast, simple, non-malodorous and suitable for scale-up.
