Organoselenium Chemistry

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