Organoselenium Chemistry

Thomas Wirth is professor of organic chemistry at Cardiff University. After studying chemistry in Bonn and at the Technical University of Berlin, he obtained his PhD in 1992 with Professor S. Blechert. After a postdoctoral stay with Professor K. Fuji at Kyoto University a JSPS fellow, he started his independent research at the University of Basel (Switzerland). In the group of Professor B. Giese he obtained his habilitationon stereoselective oxidation reactions supported by various scholarships before taking up his current position at Cardiff University in 2000. He was invited as a visiting professor to a number of places including the University of Toronto/Canada (1999), Chuo University in Tokyo/Japan (2000), and Osaka University/Japan (2004) and was awarded the Werner-Prize from the New Swiss Chemical Society (2000). His maininterests of research concern stereoselective electrophilic reactions, oxidative transformations with hypervalent iodine reagents including mechanistic investigations and organic synthesis performed in microreactors.

• Preface ELECTROPHILIC SELENIUMGeneral IntroductionAddition Reactions to Double BondsSelenocyclizations NUCLEOPHILIC SELENIUMIntroductionProperties of Selenols and SelenolatesInorganic Nucleophilic Selenium ReagentsOrganic Nucleophilic Selenium Reagents SELENIUM COMPOUNDS IN RADICAL REACTIONSHomolytic Substitution at Selenium to Generate Radical PrecursorsSelenide Building BlocksSolid-Phase SynthesisSelenide Precursors in Radical Domino ReactionsHomolytic Substitution at Selenium for the Synthesis of Se-Containing ProductsSeleno Group Transfer onto Alkenes and AlkynesPhSeH in Radical ReactionsSelenium Radical Anions, Srn1 Substitutions SELENIUM-STABILIZED CARBANIONSIntroductionPreparation of Selenium-Stabilized CarbanionsReactivity of the Selenium-Stabilized Carbanions with Electrophiles and Synthetic Transformations of the ProductsStereochemical AspectsApplication of Selenium-Stabilized Carbanions in Total SynthesisConclusion SELENIUM COMPOUNDS WITH VALENCY HIGHER THAN TWOIntroductionTrivalent, Dicoordinated Selenonium SaltsTrivalent, Tricoordinated DerivativesTetravalent, Dicoordinated DerivativesTetravalent, Tricoordinated DerivativesPentavalent DerivativesHexavalent, Tetracoordinated DerivativesHypervalent Derivatives SELENOCARBONYLSOverviewTheoretical Aspects of SelenocarbonylsMolecular Structure of SelenocarbonylsSynthetic Procedures of SelenocarbonylsManipulation of SelenocarbonylsMetal Complexes of SelenocarbonylsFuture Aspects SELENOXIDE ELIMINATION AND [2,3]-SIGMATROPIC REARRANGEMENTIntroductionPreparation and Properties of Chiral SelenoxidesSelenoxide Elimination[2,3]-Sigmatropic Rearrangement via Allylic Selenoxides[2,3]-Sigmatropic Rearrangement via Allylic Selenimides[2,3]-Sigmatropic Rearrangement via Allylic Selenium YlidesSummary SELENIUM COMPOUNDS AS LIGANDS AND CATALYSTSIntroductionSelenium-Catalyzed Reactions BIOLOGICAL AND BIOCHEMICAL ASPECTS OF SELENIUM COMPOUNDSIntroductionBiological Importance of SeleniumSelenocysteine: The 21st Amino AcidBiosynthesis of SelenocysteineChemical Synthesis of SelenocysteineChemical Synthesis of Sec-Containing Proteins and PeptidesSelenoenzymesSummary