Keywords:
Organoselenium compounds.
;
Organoselenium Compounds.
;
Composés organoséléniés.
;
Organoselenium compounds. (OCoLC)fst01048013.
;
Electronic books.
Type of Medium:
Online Resource
Pages:
1 online resource (464 pages)
Edition:
1st ed.
ISBN:
9783527641963
URL:
https://ebookcentral.proquest.com/lib/geomar/detail.action?docID=843679
DDC:
547.05724
Language:
English
Note:
Intro -- Organoselenium Chemistry: Synthesis and Reactions -- Contents -- Preface -- List of Contributors -- 1: Electrophilic Selenium -- 1.1 General Introduction -- 1.1.1 Synthesis of Electrophilic Selenium Reagents -- 1.1.2 Reactivity and Properties -- 1.2 Addition Reactions to Double Bonds -- 1.2.1 Addition Reaction Involving Oxygen-Centered Nucleophiles -- 1.2.2 Addition Reaction Involving Nitrogen-Centered Nucleophiles -- 1.2.3 Addition Reactions Involving Carbon-Centered Nucleophiles -- 1.2.4 Addition Reaction Involving Chiral Nucleophiles or Chiral Substrates -- 1.3 Selenocyclizations -- 1.3.1 Oxygen Nucleophiles -- 1.3.2 Nitrogen Nucleophiles -- 1.3.3 Competition between Oxygen and Nitrogen Nucleophiles -- 1.3.4 Carbon Nucleophiles -- 1.3.5 Double Cyclization Reactions -- References -- 2: Nucleophilic Selenium -- 2.1 Introduction -- 2.1.1 Development of Nucleophilic Selenium Reagents -- 2.1.2 Examples of Recent Applications -- 2.2 Properties of Selenols and Selenolates -- 2.2.1 Electronegativity of Selenium -- 2.2.2 Tautomerism of Selenols -- 2.2.3 Nucleophilicity of Selenolates -- 2.3 Inorganic Nucleophilic Selenium Reagents -- 2.3.1 Conventional Reagents -- 2.3.2 New Reagents -- 2.4 Organic Nucleophilic Selenium Reagents -- 2.4.1 Preparation -- 2.4.2 Structure -- 2.4.3 Ammonium Selenolates (NH4+) -- 2.4.4 Selenolates of Group 1 Elements (Li, Na, K, and Cs) -- 2.4.5 Selenolates of Group 2 Elements (Mg, Ca, and Ba) -- 2.4.6 Selenolates of Group 3 Elements (Sm, Ce, Pr, Nb, and U) -- 2.4.7 Selenolates of Group 4 Elements (Ti, Zr, and Hf) -- 2.4.8 Selenolates of Group 5 Elements (V, Nb, and Ta) -- 2.4.9 Selenolates of Group 6 Elements (Mo and W) -- 2.4.10 Selenolates of Group 7 Elements (Mn and Re) -- 2.4.11 Selenolates of Group 8 Elements (Fe, Ru, and Os) -- 2.4.12 Selenolates of Group 9 Elements (Co, Rh, and Ir).
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2.4.13 Selenolates of Group 10 Elements (Ni, Pd, and Pt) -- 2.4.14 Selenolates of Group 11 Elements (Cu, Ag, and Au) -- 2.4.15 Selenolates of Group 12 Elements (Zn, Cd, and Hg) -- 2.4.16 Selenolates of Group 13 Elements (B, Al, Ga, and In) -- 2.4.17 Selenolates of Group 14 Elements (Si, Ge, Sn, and Pb) -- 2.4.18 Selenolates of Group 15 Elements (P, As, Sb, and Bi) -- References -- 3: Selenium Compounds in Radical Reactions -- 3.1 Homolytic Substitution at Selenium to Generate Radical Precursors -- 3.1.1 Bimolecular SH2 Reactions: Synthetic Considerations -- 3.1.1.1 Radical Reagents -- 3.1.2 Alkyl Radicals from Selenide Precursors -- 3.1.3 Acyl Radicals from Acyl Selenide Precursors -- 3.1.4 Imidoyl Radicals from Imidoyl Selenides -- 3.1.5 Other Radicals from Selenide Precursors -- 3.2 Selenide Building Blocks -- 3.3 Solid-Phase Synthesis -- 3.4 Selenide Precursors in Radical Domino Reactions -- 3.5 Homolytic Substitution at Selenium for the Synthesis of Se-Containing Products -- 3.5.1 Intermolecular SH2 onto Se -- 3.5.2 Intramolecular SH2: Cyclization onto Se -- 3.6 Seleno Group Transfer onto Alkenes and Alkynes -- 3.6.1 Seleno-Selenation -- 3.6.2 Seleno-Sulfonation -- 3.6.3 Seleno-Alkylation -- 3.7 PhSeH in Radical Reactions -- 3.7.1 Radical Clock Reactions -- 3.7.2 Problem of Unwanted Trapping of Intermediate Radicals -- 3.7.3 Catalysis of Stannane-Mediated Reactions -- 3.8 Selenium Radical Anions, SRN1 Substitutions -- References -- 4: Selenium-Stabilized Carbanions -- 4.1 Introduction -- 4.2 Preparation of Selenium-Stabilized Carbanions -- 4.2.1 Deprotonation of Selenides -- 4.2.2 Element-Lithium Exchange -- 4.2.3 Conjugate Addition of Organometallics to Vinyl- and Alkynylselenides -- 4.3 Reactivity of the Selenium-Stabilized Carbanions with Electrophiles and Synthetic Transformations of the Products.
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4.3.1 Reaction of Selenium-Stabilized Carbanions with Electrophiles -- 4.3.2 Selenium-Based Transformations on the Reaction Products of Selenium-Stabilized Carbanions with Electrophiles -- 4.4 Stereochemical Aspects -- 4.4.1 Cyclic Selenium-Stabilized Carbanions -- 4.4.2 Acyclic Selenium-Stabilized Carbanions -- 4.5 Application of Selenium-Stabilized Carbanions in Total Synthesis -- 4.5.1 Examples Using Alkylation Reactions of Selenium-Stabilized Carbanions -- 4.5.2 Examples Using the Addition of Selenium-Stabilized Carbanions to Carbonyl Compounds -- 4.5.3 Examples Using 1,4-Addition of Selenium-Stabilized Carbanions to α,β-Unsaturated Carbonyl Compounds -- 4.6 Conclusion -- References -- 5: Selenium Compounds with Valency Higher than Two -- 5.1 Introduction -- 5.2 Trivalent, Dicoordinated Selenonium Salts -- 5.3 Trivalent, Tricoordinated Derivatives -- 5.4 Tetravalent, Dicoordinated Derivatives -- 5.5 Tetravalent, Tricoordinated Derivatives -- 5.6 Pentavalent Derivatives -- 5.7 Hexavalent, Tetracoordinated Derivatives -- 5.8 Hypervalent Derivatives -- 5.8.1 Selenuranes -- 5.8.2 Selenurane Oxides -- 5.8.3 Perselenuranes -- Acknowledgment -- References -- 6: Selenocarbonyls -- 6.1 Overview -- 6.2 Theoretical Aspects of Selenocarbonyls -- 6.3 Molecular Structure of Selenocarbonyls -- 6.4 Synthetic Procedures of Selenocarbonyls -- 6.5 Manipulation of Selenocarbonyls -- 6.6 Metal Complexes of Selenocarbonyls -- 6.7 Future Aspects -- References -- 7: Selenoxide Elimination and [2,3]-Sigmatropic Rearrangement -- 7.1 Introduction -- 7.2 Preparation and Properties of Chiral Selenoxides -- 7.3 Selenoxide Elimination -- 7.3.1 Enantioselective Selenoxide Elimination Producing Chiral Allenes and α,β-Unsaturated Ketones -- 7.3.2 Diastereoselective Selenoxide Elimination Producing Chiral Allenecarboxylic Esters.
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7.4 [2,3]-Sigmatropic Rearrangement via Allylic Selenoxides -- 7.4.1 Enantioselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Alcohols -- 7.4.2 Diastereoselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Alcohols -- 7.5 [2,3]-Sigmatropic Rearrangement via Allylic Selenimides -- 7.5.1 Preparation and Properties of Chiral Selenimides -- 7.5.2 Enantioselective [2,3]-Sigmatropic Rearrangement Producing Chiral Allylic Amines -- 7.5.3 Diastereoselective [2,3]-Sigmatropic Rearrangements Producing Chiral Allylic Amines -- 7.6 [2,3]-Sigmatropic Rearrangement via Allylic Selenium Ylides -- 7.6.1 Preparation and Properties of Optically Active Selenium Ylides -- 7.6.2 Enantioselective [2,3]-Sigmatropic Rearrangements via Allylic Selenium Ylides -- 7.6.3 Diastereoselective [2,3]-Sigmatropic Rearrangement via Allylic Selenium Ylides -- 7.7 Summary -- References -- 8: Selenium Compounds as Ligands and Catalysts -- 8.1 Introduction -- 8.2 Selenium-Catalyzed Reactions -- 8.2.1 Stereoselective Addition of Diorganozinc Reagents to Aldehydes -- 8.2.1.1 Diethylzinc Addition -- 8.2.1.2 Diphenylzinc Addition -- 8.2.2 Selenium-Ligated Transition Metal-Catalyzed Reactions -- 8.2.2.1 Selenium-Ligated Stereoselective Hydrosilylation of Ketones -- 8.2.2.2 Selenium-Ligated Copper-Catalyzed Addition of Organometallic Reagents to Enones -- 8.2.2.3 Selenium-Ligated Palladium-Catalyzed Asymmetric Allylic Alkylation -- 8.2.2.4 Selenium-Ligands in Palladium-Catalyzed Mizoroki-Heck Reactions -- 8.2.2.5 Selenium-Ligands in Palladium-Catalyzed Phenylselenenylation of Organohalides -- 8.2.2.6 Selenium-Ligands in Palladium-Catalyzed Substitution Reactions -- 8.2.2.7 Selenium-Ligands in the Palladium-Catalyzed Allylation of Aldehydes -- 8.2.2.8 Selenium-Ligands in Palladium-Catalyzed Condensation Reactions.
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8.2.2.9 Ruthenium-Catalyzed Substitution Reactions -- 8.2.2.10 Selenium-Ligands in Zinc-Catalyzed Intramolecular Hydroaminations -- 8.2.3 Selenium-Ligands in Organocatalytic Asymmetric Aldol Reactions -- 8.2.4 Selenium-Ligands in Stereoselective Darzens Reactions -- 8.2.5 Selenium-Catalyzed Carbonylation Reactions -- 8.2.6 Selective Reduction of α,β-Unsaturated Carbonyl Compounds -- 8.2.7 Selenium-Catalyzed Halogenations and Halocyclizations -- 8.2.8 Selenium-Catalyzed Staudinger-Vilarrasa Reaction -- 8.2.9 Selenium-Catalyzed Elimination Reactions of Diols -- 8.2.10 Selenium-Catalyzed Hydrostannylation of Alkenes -- 8.2.11 Selenium-Catalyzed Radical Chain Reactions -- 8.2.12 Selenium-Catalyzed Oxidation Reactions -- 8.2.12.1 Selenium-Catalyzed Epoxidation of Alkenes -- 8.2.12.2 Selenium-Catalyzed Dihydroxylation of Alkenes -- 8.2.12.3 Selenium-Catalyzed Oxidation of Alcohols -- 8.2.12.4 Baeyer-Villiger Oxidation -- 8.2.12.5 Selenium-Catalyzed Allylic Oxidation of Alkenes -- 8.2.12.6 Selenium-Catalyzed Oxidation of Aryl Alkyl Ketones -- 8.2.12.7 Selenium-Catalyzed Oxidation of Primary Aromatic Amines -- 8.2.12.8 Selenium-Catalyzed Oxidation of Alkynes -- 8.2.12.9 Selenium-Catalyzed Oxidation of Halide Anions -- 8.2.13 Stereoselective Catalytic Selenenylation-Elimination Reactions -- 8.2.14 Selenium-Catalyzed Diels-Alder Reactions -- 8.2.15 Selenium-Catalyzed Synthesis of Thioacetals -- 8.2.16 Selenium-Catalyzed Baylis-Hillman Reaction -- References -- 9: Biological and Biochemical Aspects of Selenium Compounds -- 9.1 Introduction -- 9.2 Biological Importance of Selenium -- 9.3 Selenocysteine: The 21st Amino Acid -- 9.4 Biosynthesis of Selenocysteine -- 9.5 Chemical Synthesis of Selenocysteine -- 9.6 Chemical Synthesis of Sec-Containing Proteins and Peptides -- 9.7 Selenoenzymes -- 9.7.1 Glutathione Peroxidases -- 9.7.2 Iodothyronine Deiodinase.
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9.7.3 Synthetic Mimics of IDs.
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