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Lithium Compounds in Organic Synthesis : From Fundamentals to Applications.
This unique book covers fundamentals of organolithium compounds and gives a comprehensive overview of the latest synthetic advances and developments in the field. Part I covers computational and spectroscopic aspects as well as structure-reactivity relationships of organolithiums, whereas Part II de...
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Otros Autores: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Hoboken :
Wiley,
2014.
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| Temas: | |
| Acceso en línea: | Texto completo |
MARC
| LEADER | 00000cam a2200000 i 4500 | ||
|---|---|---|---|
| 001 | EBOOKCENTRAL_ocn871781411 | ||
| 003 | OCoLC | ||
| 005 | 20240329122006.0 | ||
| 006 | m o d | ||
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| 008 | 140306s2014 xx o 000 0 eng d | ||
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| 049 | |a UAMI | ||
| 100 | 1 | |a Luisi, Renzo. | |
| 245 | 1 | 0 | |a Lithium Compounds in Organic Synthesis : |b From Fundamentals to Applications. |
| 260 | |a Hoboken : |b Wiley, |c 2014. | ||
| 300 | |a 1 online resource (571 pages) | ||
| 336 | |a text |b txt |2 rdacontent | ||
| 337 | |a computer |b c |2 rdamedia | ||
| 338 | |a online resource |b cr |2 rdacarrier | ||
| 588 | 0 | |a Print version record. | |
| 520 | |a This unique book covers fundamentals of organolithium compounds and gives a comprehensive overview of the latest synthetic advances and developments in the field. Part I covers computational and spectroscopic aspects as well as structure-reactivity relationships of organolithiums, whereas Part II deals with new lithium-based synthetic methodologies as well as novel synthetic applications of functionalized lithium compounds. A useful resource for newcomers and active researchers involved in organic synthesis, whether working in academia or industry! | ||
| 505 | 0 | |a Lithium Compounds in Organic Synthesis -- Contents -- List of Contributors -- Foreword -- Preface -- Part I New Structural Aspects of Lithium Compounds -- Chapter 1 Structure-Reactivity Relationship in Organolithium Compounds -- 1.1 Structural Principles in Organolithium Compounds -- 1.2 Donor-Base-Free Structures -- 1.2.1 Tetramers -- 1.2.2 Hexamers -- 1.2.3 Comparison of [Me3SiCH2Li]6 and [n-BuLi]6 -- 1.3 Disaggregation with Lewis Bases -- 1.3.1 Tetramers of Alkyllithium Compounds -- 1.3.2 Asymmetric Aggregates of [Me3SiCH2Li] (4) -- 1.3.3 An Octameric Aggregate of [Me3SiCH2Li]6 -- 1.4 Donor-Base-Induced Dimers and Monomers -- 1.4.1 Alkyllithium and Trimethylsilylmethyllithium Compounds -- 1.4.2 PMDETA Aggregated Monomers -- 1.5 Heterobimetallic Organolithium Compounds -- 1.6 Conclusion and Outlook -- References -- Further Reading -- Chapter 2 Computational Perspectives on Organolithiums -- 2.1 Introduction -- 2.2 The Nature of Bonds to Lithium -- 2.3 Aggregation of Lithium Organic Compounds -- 2.4 Solvation Effects -- 2.5 Lithium Alkoxides and Lithium Amides -- 2.6 Computational Studies on Various Organolithium Applications -- 2.7 Conclusion and Outlook -- References -- Further Reading -- Chapter 3 Spectroscopic Advances in Organolithium Reactivity: The Contribution of Rapid-Injection NMR (RINMR) -- 3.1 Introduction -- 3.2 The Curtin-Hammett Principle -- 3.3 Organolithium NMR -- 3.4 Features of RINMR -- 3.4.1 Brief History -- 3.4.2 Apparatus Descriptions and Rapidity of Acquisition -- 3.4.3 Temperature Range and Control -- 3.4.4 Volume Accuracy of Injection -- 3.5 Use of RINMR to Study Organometallic Reactions -- 3.5.1 n-Butyllithium Aggregate Reactivity (1985) -- 3.5.2 Magnesium Chelates in Carbonyl Additions (1987/1990) -- 3.5.3 Lithium Enolate Aldol (1992). | |
| 505 | 8 | |a 3.5.4 Alkyllithium Polymerization (1995/1999) -- 3.5.5 Tin Transmetallation (2007) -- 3.5.6 Cuprates (2002-Present) -- 3.5.7 n-BuLi Aggregate Reactivity Revisited (2007) -- 3.5.8 Tris(trimethylsilyl)methyllithium (2008/2009) -- 3.5.9 Enolization and Lithium Aldol (2011) -- 3.6 Conclusion and Outlook -- References -- Further Reading -- Chapter 4 Spectroscopic Advances in Structural Lithium Chemistry: Diffusion-Ordered Spectroscopy and Solid-State NMR -- 4.1 General Introduction -- 4.2 Application of Solution NMR to the Structural Characterization of Organolithium Compounds -- 4.2.1 Diffusion NMR Measurement Methods -- 4.2.1.1 Pulsed Field Gradient Spin Echo (PFGSE) -- 4.2.1.2 From the First to the Second Dimension: DOSY NMR Experiment -- 4.2.2 DOSY Application to the Structural Analysis of Organolithium Compounds -- 4.2.2.1 Structure of the Mixed Methyllithium/Lithium Chloride Aggregate -- 4.2.2.2 Structure of a Lithium Phosphido-Borane -- 4.2.2.3 Structure of Lithium Zincate -- 4.2.3 Conclusion -- 4.3 Solid-State NMR -- 4.3.1 Basic Principles -- 4.3.1.1 Homo and Heteronuclear Dipole-Dipole Couplings (D: Dipole-Dipole) -- 4.3.1.2 Chemical Shift Anisotropy (CSA) -- 4.3.1.3 Quadrupolar Interactions for Nuclei with I<1/2 (Q) -- 4.3.1.4 Magic Angle Spinning (MAS) -- 4.3.1.5 High-Power Heteronuclear Decoupling -- 4.3.1.6 Cross Polarization -- Hartmann-Hahn Condition -- 4.3.2 Solid-State NMR -- Applications to Organolithium Compounds -- 4.3.2.1 Structure of Lithium Alkyl and Aryl Complexes Stabilized by Nitrogen Ligands -- 4.3.2.2 Symmetry and Geometry of Formed Structures: CIP, SSIP, Sandwich -- 4.3.2.3 Molecular Dynamics -- 4.3.2.4 Reaction Monitoring -- 4.3.3 Conclusion and Outlook -- References -- Further Reading. | |
| 590 | |a ProQuest Ebook Central |b Ebook Central Academic Complete | ||
| 650 | 0 | |a Cyclic compounds. | |
| 650 | 0 | |a Lithium compounds. | |
| 650 | 0 | |a Organic compounds |x Synthesis. | |
| 650 | 2 | |a Lithium Compounds | |
| 650 | 6 | |a Composés cycliques. | |
| 650 | 6 | |a Lithium |x Composés. | |
| 650 | 6 | |a Composés organiques |x Synthèse. | |
| 650 | 7 | |a Cyclic compounds |2 fast | |
| 650 | 7 | |a Lithium compounds |2 fast | |
| 650 | 7 | |a Organic compounds |x Synthesis |2 fast | |
| 700 | 1 | |a Capriati, Vito. | |
| 758 | |i has work: |a Lithium Compounds in Organic Synthesis [electronic resource] (Text) |1 https://id.oclc.org/worldcat/entity/E39PCXTMDvbxcXdc8mK6bCXVvd |4 https://id.oclc.org/worldcat/ontology/hasWork | ||
| 776 | 0 | 8 | |i Print version: |z 9783527333431 |
| 856 | 4 | 0 | |u https://ebookcentral.uam.elogim.com/lib/uam-ebooks/detail.action?docID=1643668 |z Texto completo |
| 880 | 8 | |6 505-00/(S |a Chapter 5 Mixed Lithium Complexes: Structure and Application in Synthesis -- 5.1 Introduction -- 5.2 Structural Chemistry of Heterometallic Lithium Complexes -- 5.2.1 Mixed Lithium-Sodium Complexes -- 5.2.2 Mixed Lithium-Potassium Complexes -- 5.2.3 Mixed Lithium-Magnesium Complexes -- 5.2.4 Mixed Lithium-Zinc Complexes -- 5.3 Structural Chemistry of Heteroanionic Lithium Complexes -- 5.4 Synthetic Applications of Lithium Magnesiates: Turbo-Grignard Reagents -- 5.5 Conclusion and Outlook -- References -- Further Reading -- Part II New Synthetic Methodologies Based on Lithium Compounds -- Chapter 6 Oxygen-Bearing Lithium Compounds in Modern Synthesis -- 6.1 Introduction -- 6.2 α-Lithiated Oxygen-Substituted Compounds -- 6.2.1 Acyclic α-Alkoxy Organolithiums -- 6.2.1.1 Nonstabilized α-Alkoxy Organolithiums -- 6.2.1.2 Dipole-Stabilized α-Alkoxy Organolithiums -- 6.2.2 Cyclic α-Alkoxy Organolithiums -- 6.2.2.1 α-Lithiated Oxiranes -- 6.2.2.2 α-Lithiated Oxetanes -- 6.2.2.3 Miscellaneous -- 6.3 ortho-Lithiated Oxygen-Bearing Aromatic Compounds -- 6.4 Remote Lithiated Oxygen-Bearing Compounds -- 6.5 Conclusion and Outlook -- References -- Further Reading -- Chapter 7 Nitrogen-Bearing Lithium Compounds in Modern Synthesis -- 7.1 Introduction -- 7.2 Lithiation of Cyclic Amines -- 7.2.1 Three-Membered Rings: Lithiated Aziridines -- 7.2.2 Four-Membered Rings: Lithiated Azetidines -- 7.2.3 Five-Membered Rings: Lithiated Pyrrolidines -- 7.2.4 Six-Membered Rings: Lithiated Piperidines -- 7.2.5 Seven-Membered Rings: Lithiated Azepines -- 7.2.6 Amino-Organolithiums from Heterocycles with More Than One Nitrogen Atom -- 7.3 Lithiation of Acyclic Amines -- 7.4 Conclusion and Outlook -- References -- Further Reading -- Chapter 8 Sulfur-Bearing Lithium Compounds in Modern Synthesis -- 8.1 Introduction -- 8.2 α-Lithiation -- 8.2.1 Thioethers. | |
| 880 | 8 | |6 505-00/(S |a 8.2.2 Sulfoxides -- 8.2.2.1 Alkyl Carbanions -- 8.2.2.2 Vinylic Carbanions -- 8.2.3 α-Sulfones -- 8.2.4 α-Sulfoximines -- 8.3 β-Lithiation (ortho-Directed Lithiation) -- 8.3.1 Sulfides -- 8.3.2 Sulfoxides -- 8.3.3 Sulfones and Sulfonamides -- 8.3.4 Sulfoximines -- 8.4 γ-Lithiation -- 8.4.1 Lateral Lithiation -- 8.4.1.1 Sulfoxides -- 8.4.1.2 Other Aryl Thioderivatives -- 8.4.2 Nitrogenated Fragments -- 8.5 Conclusion and Outlook -- References -- Further Reading -- Chapter 9 Phosphorus-Bearing Lithium Compounds in Modern Synthesis -- 9.1 Introduction -- 9.2 Carbanions Directly Linked to a Phosphorus Atom: PC1Li -- 9.2.1 PC1Li Species via Cα-Lithiation of P(III) Compounds -- 9.2.2 PC1Li Species via Cα-Lithiation of P(V) Compounds -- 9.2.3 PC1Li Species via Reactions of α, β-Unsaturated P(V) Compounds -- 9.3 Carbanions Separated by One Atom from the Phosphorus: PC2Li -- 9.3.1 PC2Li Species via XCα-Lithiation (X = N, O) of P(V) Compounds -- 9.3.2 PC2Li Species via ortho-Lithiation of Organophosphorus Compounds -- 9.4 Carbanions Separated by Three Bonds from a Phosphorus Atom: PC3Li -- 9.5 Conclusion and Outlook -- References -- Further Reading -- Chapter 10 Advances in the Chemistry of Chiral Lithium Amides -- 10.1 Introduction -- 10.2 Chiral Lithium Amides as Bases -- 10.2.1 Enantioselective Conversion of Epoxides into Allylic Alcohols -- 10.2.2 Enantioselective Deprotonation of Cyclic Prochiral Ketones -- 10.2.3 Enantioselective Deprotonation of Bridgehead Carbons -- 10.2.4 Enantioselective Deprotonation of Benzylic Positions -- 10.2.5 Other Reactions -- 10.3 Chiral Lithium Amides as Nucleophiles -- 10.4 Chiral Lithium Amides as Ligands -- 10.5 Chiral Lithium Amides Structures -- 10.6 Conclusion and Outlook -- References -- Chapter 11 Advances in Carbolithiation. | |
| 880 | 8 | |6 505-00/(S |a 11.1 Introduction: The Definition of the Carbolithiation Reaction -- 11.2 Intermolecular Carbolithiation of Alkenes -- 11.3 Intramolecular Carbolithiation of Alkenes -- 11.4 Intermolecular Carbolithiation of Alkynes -- 11.5 Intramolecular Carbolithiation of Alkynes -- 11.6 Conclusion and Outlook -- References -- Further Reading -- Chapter 12 Reductive Lithiation and Multilithiated Compounds in Synthesis -- 12.1 Introduction -- 12.2 Alternative Solvents for Reductive Lithiation Reactions -- 12.3 Reductive Lithiation of Heterocyclic Compounds -- 12.4 Reductive Lithiation via C-C Bond Cleavage -- 12.5 Ammonia-Free Birch Reductions -- 12.6 Silyl-Lithium Derivatives -- References -- Further Reading -- Chapter 13 Dearomatization and Aryl Migration in Organolithium Chemistry -- 13.1 Introduction -- 13.2 Intermolecular Dearomatizing Addition Reactions -- 13.3 Intramolecular Dearomatizing Cyclization Reactions -- 13.3.1 Additions to Aryloxazolines -- 13.3.2 Additions to Arylsulfones -- 13.3.3 Additions to Aromatic Sulfonamides and Phosphonamides -- 13.3.4 Additions to Aromatic Amides -- 13.3.5 "Pericyclic" Dearomatizations -- 13.4 Aryl Migrations -- 13.4.1 Aryl Migration in N-aryl Ureas -- 13.4.2 Aryl Migration in N-aryl Carbamates -- 13.4.3 Aryl Migration in N-aryl Thiocarbamates -- 13.5 Alkenyl Migrations -- 13.6 Conclusion and Outlook -- References -- Chapter 14 Lithium-Boron Chemistry: A Synergistic Strategy in Modern Synthesis -- 14.1 Reagent-Controlled Lithiation-Borylation -- 14.2 α-Halogen-Stabilized Lithium Carbenoids -- 14.3 Alkylidene-Type Carbenoids -- 14.4 α-Oxygen-Stabilized Organolithiums -- 14.4.1 α-Lithiated Primary Carbamates -- 14.4.2 α-Lithiated Benzoate Esters -- 14.4.3 α-Lithiated Benzylic Carbamates -- 14.4.4 α-Lithiated Allylic Carbamates -- 14.4.5 α-Lithiated Epoxides -- 14.5 α-Nitrogen-Stabilized Organolithiums. | |
| 880 | 8 | |6 505-00/(S |a 14.5.1 α-Lithiated Aziridines. | |
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