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Synthesis of Organoselenium Compounds

Organic Selenium and Tellurium (2013)

  1. Sanjio S. Zade1,2,
  2. Harkesh B. Singh3

Published Online: 22 OCT 2012

DOI: 10.1002/9780470682531.pat0706

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Zade, S. S. and Singh, H. B. 2012. Synthesis of Organoselenium Compounds. Patai's Chemistry of Functional Groups. .

Author Information

  1. 1

    Department of Chemical Sciences, Indian Institute of Science Education and Research, Kolkata, India

  2. 2

    West Bengal, Nadia, India

  3. 3

    Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, India

Publication History

  1. Published Online: 22 OCT 2012

Abstract

In this chapter the major advances in the synthetic methodology and the syntheses of novel organoselenium compounds-since 1987 are reviewed. These are presented in the order of oxidation states i.e. in the initial parts of the chapter developments in the area of the synthesis of low valent organoselenium compounds are discussed. These include: diselenides, selenides, selenols, selenolesters, selenones, selenocyanate, selenenyl halides and related derivatives. The latter part of the chapter deals with the syntheses of high valent i.e. selenium (IV) and selenium (VI) compounds.

Diselenides are generally prepared by the reaction of alkali metal chalcogenolates with appropriate organic halides. There has been a lot of activity in the area of the synthesis of selenides. The procedures include: epoxide ring opening, aziridine and other ring opening, addition to double and triple bonds, transition metal and Main Group Element catalyzed coupling reactions, nucleophilic substitution reactions, etc.

The novel compounds described include: selenocystine derivatives, chiral diselenides, triselenides, oranoselenenyl cations, selenium-containing pincer ligands for catalysis, selenols and nitrososelenol derivatives, selenenyl azides. The chapter is based on over 350 original references.

Keywords:

  • organoselenium compounds;
  • diselenides;
  • selenides;
  • selenols;
  • selenolesters;
  • selenones;
  • selenocyanates;
  • selenenyl halides;
  • selenium (IV) compounds