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

Organic Selenium and Tellurium (2013)

  1. Vladimir A. Potapov

Published Online: 17 JUN 2013

DOI: 10.1002/9780470682531.pat0716

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Potapov, V. A. 2013. Organic Diselenides, Ditellurides, Polyselenides and Polytellurides. Synthesis and Reactions. Patai's Chemistry of Functional Groups. .

Author Information

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, RUS-664033 Irkutsk, Russian Federation

Publication History

  1. Published Online: 17 JUN 2013

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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.

Keywords:

  • diselenides;
  • ditellurides;
  • triselenides;
  • tritellurides;
  • polyselenides;
  • polytellurides;
  • selenium;
  • tellurium