Wirth Organoselenium Chemistry

Synthesis and Reactions
1. Auflage 2011
ISBN: 978-3-527-64196-3
Verlag: Wiley-VCH
Format: PDF
Kopierschutz: Adobe DRM (»Systemvoraussetzungen)

E-Book, Englisch, 448 Seiten, E-Book

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

Autoren/Hrsg.

Wirth, Thomas

Inhaltsverzeichnis

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

Über Autor(innen)

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 habilitation

on 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 main

interests of research concern stereoselective electrophilic reactions, oxidative transformations with hypervalent iodine reagents including mechanistic investigations and organic synthesis performed in microreactors.