Organoselenium Chemistry

Selenium-based methods in synthetic chemistry have developed rapidly over the past years and are now offering highly useful tools for organic synthesis. Filling the gap for a comprehensive handbook and ready reference, this book covers all modern developments within

the field, including biochemical aspects. The chemistry chapters are organized according to the different reactivities of various selenium

compounds and reagents, with each chapter dealing with a special reaction type.

 

Also includes a table with 77Se NMR shifts to aid in practical problems.

 

From the Contents:

* Electrophilic and Nucleophilic Selenium

* Selenium Compounds in Radical Reactions

* Selenium-Stabilized Carbanions

* Selenium Compounds with Valency Higher than Two

* Selenocarbonyls

* Selenoxide Elimination and [2,3]-Sigmatropic Rearrangement

* Selenium Compounds as Ligands and Catalysts

* Biological and Biochemical Aspects of Selenium Compounds

Preface
 
ELECTROPHILIC SELENIUM
General Introduction
Addition Reactions to Double Bonds
Selenocyclizations
 
NUCLEOPHILIC SELENIUM
Introduction
Properties of Selenols and Selenolates
Inorganic Nucleophilic Selenium Reagents
Organic Nucleophilic Selenium Reagents
 
SELENIUM COMPOUNDS IN RADICAL REACTIONS
Homolytic Substitution at Selenium to Generate Radical Precursors
Selenide Building Blocks
Solid-Phase Synthesis
Selenide Precursors in Radical Domino Reactions
Homolytic Substitution at Selenium for the Synthesis of Se-Containing Products
Seleno Group Transfer onto Alkenes and Alkynes
PhSeH in Radical Reactions
Selenium Radical Anions, Srn1 Substitutions
 
SELENIUM-STABILIZED CARBANIONS
Introduction
Preparation of Selenium-Stabilized Carbanions
Reactivity of the Selenium-Stabilized Carbanions with Electrophiles and Synthetic Transformations of the Products
Stereochemical Aspects
Application of Selenium-Stabilized Carbanions in Total Synthesis
Conclusion
 
SELENIUM COMPOUNDS WITH VALENCY HIGHER THAN TWO
Introduction
Trivalent, Dicoordinated Selenonium Salts
Trivalent, Tricoordinated Derivatives
Tetravalent, Dicoordinated Derivatives
Tetravalent, Tricoordinated Derivatives
Pentavalent Derivatives
Hexavalent, Tetracoordinated Derivatives
Hypervalent Derivatives
 
SELENOCARBONYLS
Overview
Theoretical Aspects of Selenocarbonyls
Molecular Structure of Selenocarbonyls
Synthetic Procedures of Selenocarbonyls
Manipulation of Selenocarbonyls
Metal Complexes of Selenocarbonyls
Future Aspects
 
SELENOXIDE ELIMINATION AND [2,3]-SIGMATROPIC REARRANGEMENT
Introduction
Preparation and Properties of Chiral Selenoxides
Selenoxide Elimination
[2,3]-Sigmatropic Rearrangement via Allylic Selenoxides
[2,3]-Sigmatropic Rearrangement via Allylic Selenimides
[2,3]-Sigmatropic Rearrangement via Allylic Selenium Ylides
Summary
 
SELENIUM COMPOUNDS AS LIGANDS AND CATALYSTS
Introduction
Selenium-Catalyzed Reactions
 
BIOLOGICAL AND BIOCHEMICAL ASPECTS OF SELENIUM COMPOUNDS
Introduction
Biological Importance of Selenium
Selenocysteine: The 21st Amino Acid
Biosynthesis of Selenocysteine
Chemical Synthesis of Selenocysteine
Chemical Synthesis of Sec-Containing Proteins and Peptides
Selenoenzymes
Summary

• Edited by Thomas Wirth