Organoselenium Chemistry: Synthesis and Reactions
有机硒化学：合成与反应
Editor: Thomas Wirth
Publisher: John Wiley and Sons, 2012
Print IN: 978-3-527-32944-1
ePDF IN: 978-3-527-64196-3
Format: PDF；File Size: 3.93MB；Page: 457
Contents
Preface XI
List of Contributor XIII
1 Electrophilic Selenium 1
1.1 General Introduction 1
1.2 Addition Reactions to Double Bonds 11
1.3 Selenocyclizations 30
References 45
2 Nucleophilic Selenium 53
2.1 Introduction 53
2.2 Properties of Selenols and Selenolates 56
2.3 Inorganic Nucleophilic Selenium Reagents 59
2.4 Organic Nucleophilic Selenium Reagents 65
References 102
3 Selenium Compounds in Radical Reactions 111
3.1 Homolytic Substitution at Selenium to Generate Radical Precursors 111
3.2 Selenide Building Blocks 126
3.3 Solid-Phase Synthesis 128
3.4 Selenide Precursors in Radical Domino Reactions 130
3.5 Homolytic Substitution at Selenium for the Synthesis of Se-Containing Products 132
3.6 Seleno Group Transfer onto Alkenes and Alkynes 134
3.7 PhSeH in Radical Reactions 138
3.8 Selenium Radical Anions, SRN1 Substitutions 141
References 143
4 Selenium-Stabilized Carbanions 147
4.1 Introduction 147
4.2 Preparation of Selenium-Stabilized Carbanions 149
4.3 Reactivity of the Selenium-Stabilized Carbanions with Electrophiles and Synthetic Transformations of the Products 161
4.4 Stereochemical Aspects 168
4.5 Application of Selenium-Stabilized Carbanions in Total Synthesis 176
4.6 Conclusion 186
References 187
5 Selenium Compounds with Valency Higher than Two 191
5.1 Introduction 191
5.2 Trivalent, Dicoordinated Selenonium Salts 192
5.3 Trivalent, Tricoordinated Derivatives 194
5.4 Tetravalent, Dicoordinated Derivatives 211
5.5 Tetravalent, Tricoordinated Derivatives 225
5.6 Pentavalent Derivatives 239
5.7 Hexavalent, Tetracoordinated Derivatives 240
5.8 Hypervalent Derivatives 244
References 251
6 Selenocarbonyls 257
6.1 Overview 257
6.2 Theoretical Aspects of Selenocarbonyls 259
6.3 Molecular Structure of Selenocarbonyls 261
6.4 Synthetic Procedures of Selenocarbonyls 261
6.5 Manipulation of Selenocarbonyls 270
6.6 Metal Complexes of Selenocarbonyls 278
6.7 Future Aspects 280
References 281
7 Selenoxide Elimination and [2,3]-Sigmatropic Rearrangement 287
7.1 Introduction 287
7.2 Preparation and Properties of Chiral Selenoxides 288
7.3 Selenoxide Elimination 292
7.4 [2,3]-Sigmatropic Rearrangement via Allylic Selenoxides 297
7.5 [2,3]-Sigmatropic Rearrangement via Allylic Selenimides 305
7.6 [2,3]-Sigmatropic Rearrangement via Allylic Selenium Ylides 311
7.7 Summary 317
References 317
8 Selenium Compounds as Ligands and Catalysts 321
8.1 Introduction 321
8.2 Selenium-Catalyzed Reactions 321
References 356
9 Biological and Biochemical Aspects of Selenium Compounds 361
9.1 Introduction 361
9.2 Biological Importance of Selenium 361
9.3 Selenocysteine: The 21st Amino Acid 362
9.4 Biosynthesis of Selenocysteine 363
9.5 Chemical Synthesis of Selenocysteine 366
9.6 Chemical Synthesis of Sec-Containing Proteins and Peptides 367
9.7 Selenoenzymes 369
9.8 Summary 389
References 392
77Se NMR Values 397
Index 435
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