Organoselenium chemistry : synthesis and reactions

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Organoselenium chemistry : synthesis and reactions / edited by Thomas Wirth

資料種別:: 図書
出版情報:: Weinheim : Wiley-VCH, c2012
形態:: xiv, 448 p. ; 25 cm
著者名:: Wirth, Thomas
ISBN:: 9783527329441 [3527329447]
書誌ID:: BB08055801

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注記:

Includes bibliographical references and index

主題:

Organoselenium compounds

言語:

英語

目次情報:

Preface

List of Contributor

Electrophilic Selenium / Claudio Santi ; Stefano Santoro1：

General Introduction / 1.1：

Synthesis of Electrophilic Selenium Reagents / 1.1.1：

Reactivity and Properties / 1.1.2：

Addition Reactions to Double Bonds / 1.2：

Addition Reaction Involving Oxygen Centered Nucleophiles / 1.2.1：

Addition Reaction Involving Nitrogen Centered Nucleophiles / 1.2.2：

Addition Reactions Involving Carbon Centered Nucleophiles / 1.2.3：

Addition Reaction Involving Chiral Nucleophiles or Chiral Substrates / 1.2.4：

Selenocyclizations / 1.3：

Oxygen Nucleophiles / 1.3.1：

Nitrogen Nucleophiles / 1.3.2：

Competition between Oxygen and Nitrogen Nucleophiles / 1.3.3：

Carbon Nucleophiles / 1.3.4：

Double Cyclization Reactions / 1.3.5：

References

Nucleophilic Selenium / Michio Iwaoka2：

Introduction / 2.1：

Development of Nucleophilic Selenium Reagents / 2.1.1：

Examples of Recent Applications / 2.1.2：

Properties of Selenols and Selenolates / 2.2：

Electronegativity of Selenium / 2.2.1：

Tautomerism of Selenols / 2.2.2：

Nudeophilicity of Selenolates / 2.2.3：

Inorganic Nucleophilic Selenium Reagents / 2.3：

Conventional Reagents / 2.3.1：

New Reagents / 2.3.2：

Organic Nucleophilic Selenium Reagents / 2.4：

Preparation / 2.4.1：

Structure / 2.4.2：

Ammonium Selenolates (NH4+) / 2.4.3：

Selenolates of Group 1 Elements (Li, Na, K, and Cs) / 2.4.4：

Selenolates of Group 2 Elements (Mg, Ca, and Ba) / 2.4.5：

Selenolates of Group 3 Elements (Sm, Ce, Pr, Nb, and U) / 2.4.6：

Selenolates of Group 4 Elements (Ti, Zr, and Hf) / 2.4.7：

Selenolates of Group 5 Elements (V, Nb, and Ta) / 2.4.8：

Selenolates of Group 6 Elements (Mo and W) / 2.4.9：

Selenolates of Group 7 Elements (Mn and Re) / 2.4.10：

Selenolates of Group 8 Elements (Fe,Ru, and Os) / 2.4.11：

Selenolates of Group 9 Elements (Co, Rh, and Ir) / 2.4.12：

Selenolates of Group 10 Elements (Ni,Pd, and Pt) / 2.4.13：

Selenolates of Group 11 Elements (Cu, Ag, and Au) / 2.4.14：

Selenolates of Group 12 Elements (Zn, Cd, and Hg) / 2.4.15：

Selenolates of Group 13 Elements (B, Al, Ga, and In) / 2.4.16：

Selenolates of Group 14 Elements (Si, Ge, Sn, and Pb) / 2.4.17：

Selenolates of Group 15 Elements (P, As, Sb, and Bi) / 2.4.18：

Selenium Compounds in Radical Reactions / W. Russell Bowman3：

Homolytic Substitution at Selenium to Generate Radical Precursors / 3.1：

Bimolecular S_H2 Reactions: Synthetic Considerations / 3.1.1：

Radical Reagents / 3.1.1.1：

Alkyl Radicals from Selenide Precursors / 3.1.2：

Acyl Radicals from Acyl Selenide Precursors / 3.1.3：

Imidoyl Radicals from Imidoyl Selenides / 3.1.4：

Other Radicals from Selenide Precursors / 3.1.5：

Selenide Building Blocks / 3.2：

Solid Phase Synthesis / 3.3：

Selenide Precursors in Radical Domino Reactions / 3.4：

Homolytic Substitution at Selenium for the Synthesis of Se Containing Products / 3.5：

Intermolecular S_H2 onto Se / 3.5.1：

Intramolecular S_H2: Cyclization onto Se / 3.5.2：

Seleno Group Transfer onto Alkenes and Alkynes / 3.6：

Seleno Selenation / 3.6.1：

Seleno Sulfonation / 3.6.2：

Seleno Alkylation / 3.6.3：

PhSeH in Radical Reactions / 3.7：

Radical Clock Reactions / 3.7.1：

Problem of Unwanted Trapping of Intermediate Radicals / 3.7.2：

Catalysis of Starrnane-Mediated Reactions / 3.7.3：

Selenium Radical Anions, S_RN1 Substitutions / 3.8：

Selenium Stabilized Carbanions / Joao V. Comasseto ; Alcindo A. Dos Santos ; Edison P. Wendler4：

Preparation of Selenium-Stabilized Carbanions / 4.1：

Deprotonation of Selenides / 4.2.1：

Element Lithium Exchange / 4.2.2：

Conjugate Addition of Organometallics to Vinyl and Alkynylselenides / 4.2.3：

Reactivity of the Selenium-Stabilized Carbanions with Electrophiles and Synthetic Transformations of the Products / 4.3：

Reaction of Selernum Stabilized Carbanions with Electrophiles / 4.3.1：

Selenium Based Transformations on the Reaction Products of Selenium Stabilized Carbanions with Electrophiles / 4.3.2：

Stereochemical Aspects / 4.4：

Cyclic Selenium Stabilized Carbanions / 4.4.1：

Acyclic Selenium Stabilized Carbanions / 4.4.2：

Application of Selenium Stabilized Carbanions in Total Synthesis / 4.5：

Examples Using Alkylation Reactions of Selenium Stabilized Carbanions / 4.5.1：

Examples Using the Addition of Selenium-Stabilized Carbanions to Carbonyl Compounds / 4.5.2：

Examples Using 1,4 Addition of Selenium-Stabihzed Carbanions to a,p-Unsaturated Carbonyl Compounds / 4.5.3：

Conclusion / 4.6：

Selenium Compounds with Valency Higher than Two / Jozef Drabowicz ; Jarosiaw Lewkowski ; Jacek Scianowski5：

Trivalent, Dicoordinated Selenonium Salts / 5.1：

Trivalent, Tricoordinated Derivatives / 5.3：

Tetravalent, Dicoordinated Derivatives / 5.4：

Tetravalent, Tricoordinated Derivatives / 5.5：

Pentavalent Derivatives / 5.6：

Hexavalent, Tetracoordinated Derivatives / 5.7：

Hypervalent Derivatives / 5.8：

Selenuranes / 5.8.1：

Selenurane Oxides / 5.8.2：

Perselenuranes / 5.8.3：

Acknowledgment

Selenocarbonyls / Toshiaki Murai6：

Overview / 6.1：

Theoretical Aspects of Selenocarbonyls / 6.2：

Molecular Structure of Selenocarbonyls / 6.3：

Synthetic Procedures of Selenocarbonyls / 6.4：

Manipulation of Selenocarbonyls / 6.5：

Metal Complexes of Selenocarbonyls / 6.6：

Future Aspects / 6.7：

Selenoxide Elimination and [2,3]-Sigmatropic Rearrangement / Yoshiaki Nishibayashi ; Sakae Uemura7：

Preparation and Properties of Chiral Selenoxides / 7.1：

Selenoxide Elimination / 7.3：

Enantioselective Selenoxide Elimination Producing Chiral Allenes and Unsaturated Ketones / 7.3.1：

Diastereoselective Selenoxide Elimination Producing Chiral Allenecarboxylic Esters / 7.3.2：

2,3-Sigmatropic Rearrangement via Allylic Selenoxides / 7.4：

Enanrioselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Alcohols / 7.4.1：

Diastereoselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Alcohols / 7.4.2：

2,3-Sigmatropic Rearrangement via Allylic Selenimides / 7.5：

Preparation and Properties of Chiral Selenimides / 7.5.1：

Enanrioselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Amines / 7.5.2：

Diastereoselective [2,3]-Sigmatropic Rearrangements Producing Chiral Allylic Amines / 7.5.3：

2,3-Sigmatropic Rearrangement via Allylic Selenium Ylides / 7.6：

Preparation and Properties of Optically Active Selenium Ylides / 7.6.1：

Enantioselective [2,3]-Sigmatropic Rearrangements via Allylic Selenium Ylides / 7.6.2：

Diastereoselective [2,3]-Sigmatropic Rearrangement via Allylic Selenium Ylides / 7.6.3：

Summary / 7.7：

Selenium Compounds as Ligands and Catalysts / Fateh V. Singh ; Thomas Wirth8：

Selenium-Catalyzed Reactions / 8.1：

Stereoselective Addition of Diorganozinc Reagents to Aldehydes / 8.2.1：

Diethylzinc Addition / 8.2.1.1：

Diphenylzinc Addition / 8.2.1.2：

Selenium-Ligated Transition Metal-Catalyzed Reactions / 8.2.2：

Selenium-Ligated Stereoselective Hydrosilylation of Ketones / 8.2.2.1：

Selenium-Ligated Copper-Catalyzed Addition of Organometallic Reagents to Enones / 8.2.2.2：

Selenium-Ligated Palladium-Catalyzed Asymmetric Allylic Alkylation / 8.2.2.3：

Selenium-Ligands in Palladium-Catalyzed Mizoroki-Heck Reactions / 8.2.2.4：

Selenium-Ligands in Palladium-Catalyzed Phenylselenenylation of Organohalides / 8.2.2.5：

Selenium-Ligands in Palladium-Catalyzed Substitution Reactions / 8.2.2.6：

Selenium-Ligands in the Palladium-Catalyzed Allylation of Aldehydes / 8.2.2.7：

Selenium-Ligands in Palladium-Catalyzed Condensation Reactions / 8.2.2.8：

Ruthenium-Catalyzed Substitution Reactions / 8.2.2.9：

Selenium-Ligands in Zinc-Catalyzed Intramolecular Hydroaminations / 8.2.2.10：

Selenium-Ligands in Organocatalytic Asymmetric Aldol Reactions / 8.2.3：

Selenium-Ligands in Stereoselective Darzens Reactions / 8.2.4：

Selenium-Catalyzed Carbonylation Reactions / 8.2.5：

Selective Reduction of a,p-Unsaturated Carbonyl Compounds / 8.2.6：

Selenium-Catalyzed Halogenations and Halocyclizations / 8.2.7：

Selenium-Catalyzed Staudinger-Vilarrasa Reaction / 8.2.8：

Selenium-Catalyzed Elimination Reactions of Diols / 8.2.9：

Selenium-Catalyzed Hydrostannylation of Alkenes / 8.2.10：

Selenium-Catalyzed Radical Chain Reactions / 8.2.11：

Selenium-Catalyzed Oxidation Reactions / 8.2.12：

Selenium-Catalyzed Epoxidation of Alkenes / 8.2.12.1：

Selenium-Catalyzed Dihydroxylation of Alkenes / 8.2.12.2：

Selenium-Catalyzed Oxidation of Alcohols / 8.2.12.3：

Baeyer-Villiger Oxidation / 8.2.12.4：

Selenium-Catalyzed Allylic Oxidation of Alkenes / 8.2.12.5：

Selenium-Catalyzed Oxidation of ArylAlkyl Ketones / 8.2.12.6：

Selenium-Catalyzed Oxidation of Primary Aromatic Amines / 8.2.12.7：

Selenium-Catalyzed Oxidation of Alkynes / 8.2.12.8：

Selenium-Catalyzed Oxidation of Halide Anions / 8.2.12.9：

Stereoselective Catalytic Selenenylation-Elimination Reactions / 8.2.13：

Selenium-Catalyzed Diels-Alder Reactions / 8.2.14：

Selenium-Catalyzed Synthesis of Thioacetals / 8.2.15：

Selenium-Catalyzed Baylis-Hillman Reaction / 8.2.16：

Biological and Biochemical Aspects of Selenium Compounds / Bhaskar J. Bhuyan ; Govindasamy Mugesh9：

Biological Importance of Selenium / 9.1：

Selenocysteine: The 21st Amino Acid / 9.3：

Biosynthesis of Selenocysteine / 9.4：

Chemical Synthesis of Selenocysteine / 9.5：

Chemical Synthesis of Sec-Containing Proteins and Peptides / 9.6：

Selenoenzymes / 9.7：

Glutathione Peroxidases / 9.7.1：

Iodothyronine Deiodinase / 9.7.2：

Synthetic Mimics of IDs / 9.7.3：

Thioredoxirn Reductase / 9.7.4：

öSe NMR Values / 9.8：

Index

Preface

List of Contributor

Electrophilic Selenium / Claudio Santi ; Stefano Santoro1：

General Introduction / 1.1：

Synthesis of Electrophilic Selenium Reagents / 1.1.1：

Reactivity and Properties / 1.1.2：

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