Organic Diselenides, Ditellurides, Polyselenides and Polytellurides. Synthesis and Reactions

Abstract

Organic diselenides and ditellurides represent very important classes of compounds, which find valuable applications in organochalcogen chemistry and in organic synthesis. The review describes the main efficient and reliable approaches to organic diselenides and ditellurides and their principal chemical reactions. Examples of syntheses of tri‐ and polyselenides and ‐tellurides have been presented. Typical reactions of organic diselenides and ditellurides with nucleophiles, electrophiles, radicals, carbenes and compounds containing the element‐element bond have been discussed in the review. Regio‐ and stereoselective reactions of organic diselenides and ditellurides with unsaturated compounds provide various chalcogenyl and bis(chalcogenyl) derivatives, which are often used in further transformations including stereoselective synthesis of functionalized alkenes. Along with valuable chemical reactions, organic diselenides and ditellurides act as precursors of both nucleophilic and electrophilic selenium and tellurium species, which participate in various useful transformations. The remarkable property of reacting with high regio‐ and stereoselectivity finds widespread application of selenium and tellurium species in organic synthesis. Besides valuable synthetic applications, organic diselenides and ditellurides exhibit various biological activities including glutathione peroxidase‐like action. Aspects of biological activity of these compounds as well as a comparison of selenol–diselenide and thiol–disulfide reversible exchange reactions have been discussed in the review.

(Z,Z)-Selanediylbis(2-propenamides): Novel Class of Organoselenium Compounds with High Glutathione Peroxidase-Like Activity. Regio- and Stereoselective Reaction of Sodium Selenide with 3-Trimethylsilyl-2-propynamides

“…The commonly used conditions for generation of organylselenolates from corresponding diselenides and sodium selenide from elemental selenium consist in the application of sodium borohydride as a reducing agent and carrying out the reaction in alcohols [ 59 ]. However, when the reactions of sodium benzeneselenolate or sodium selenide with 3-(trimethylsilyl)-2-propynamides proceeded in methanol or ethanol, the formation of 3-alkoxy-2-propenamides as by-products was observed.…”

Quantum chemical calculations of77Se and125Te nuclear magnetic resonance spectral parameters and their structural applications

“…Dihedral angular dependences of 3 J(Se,H-3) and 3 J (Se,H-4) of 2-substituted selenophenes 25-28 with respect C H A R T 3 Selenophene (X = H) (19) and its 2-substituted derivatives considered in Rusakov et al [302] : X = Cl (23), CN (24), CHO (25), COCH 3 (26), COOH (27), CH NOH (28) to the internal rotation of the substituent in the second position of the selenophene ring were also calculated at the SOPPA/aug-cc-pVTZ-J level in a previous work. [302] Remarkable stereochemical behaviors of vicinal 3 J(Se,H CO ) and 3 J(Se,H CN ) SSCCs of 25 and 28 are illustrated below, in Figure 5.…”

“…[20] Chemistry of selenium and tellurium becomes more and more important in contemporary material science, synthesizing an increasing number of seleniumand tellurium-containing compounds. [21][22][23][24] Nuclear spin of ½ and favorable natural abundances of 77 Se (7.63%) [25] and 125 Te (7.07%) [25] make selenium and tellurium nuclear magnetic resonance (NMR) spectroscopy a powerful tool of structural elucidation of novel selenium and tellurium compounds in both organic and inorganic chemistry nowadays. Recent advances in selenium and tellurium NMR spectroscopy are covered in a great number of comprehensive reviews, [26][27][28][29][30][31][32] though, the reviews on quantum chemical modeling of 77 Se and 125 Te NMR spectra, have been published in a very scarce number by the moment.…”

“…[ 20 ] Chemistry of selenium and tellurium becomes more and more important in contemporary material science, synthesizing an increasing number of selenium‐ and tellurium‐containing compounds. [ 21–24 ]…”

Remarkable Alkene-to-Alkene and Alkene-to-Alkyne Transfer Reactions of Selenium Dibromide and PhSeBr. Stereoselective Addition of Selenium Dihalides to Cycloalkenes

“…Selenium is an essential trace element nutrient that functions as cofactor for glutathione peroxidase and certain forms of thioredoxin reductase in humans [1][2][3][4]. Organoselenium compounds exhibit various biological activities, including antitumor, antibacterial, antifungal, anti-inflammatory, and glutathione peroxidase-like actions [1][2][3][4][5][6][7][8][9]. Selenium-containing reagents and organoselenium compounds play an important role in modern organic synthesis [7][8][9][10][11][12][13][14].…”