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Modern nucleophilic aromatic substitution /
This book provides a comprehensive overview of nucleophilic aromatic substitutions, focusing on the mechanistic and synthetic features that govern these reactions. The first chapter presents a detailed mechanistic analysis of the factors determining the feasibility of SNAr substitutions, providing d...
| Clasificación: | Libro Electrónico |
|---|---|
| Autor principal: | |
| Formato: | Electrónico eBook |
| Idioma: | Inglés |
| Publicado: |
Weinheim ; Hoboken :
Wiley-VCH Verlag GmbH & Co. KGaA,
[2013]
|
| Temas: | |
| Acceso en línea: | Texto completo |
MARC
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| 050 | 4 | |a QD262 |b .T384 2013 | |
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| 049 | |a UAMI | ||
| 100 | 1 | |a Terrier, François. | |
| 245 | 1 | 0 | |a Modern nucleophilic aromatic substitution / |c François Terrier. |
| 264 | 1 | |a Weinheim ; |a Hoboken : |b Wiley-VCH Verlag GmbH & Co. KGaA, |c [2013] | |
| 264 | 4 | |c ©2013 | |
| 300 | |a 1 online resource (xiii, 472 pages) : |b illustrations | ||
| 336 | |a text |b txt |2 rdacontent | ||
| 337 | |a computer |b c |2 rdamedia | ||
| 338 | |a online resource |b cr |2 rdacarrier | ||
| 504 | |a Includes bibliographical references and index. | ||
| 505 | 0 | 0 | |6 880-01 |t The SnAr Reactions: Mechanistic Aspects -- |t Structure and Reactivity of Anionic [alpha]-Complexes -- |t The Superelectrophilic Dimension in SnAr and Related [alpha]-Complexation Processes -- |t Synthetic Aspects of Intermolecular SnAr Reactions -- |t Intramolecular SnAr Reactions -- |t Nucleophilic Aromatic Substitutions of Hydrogen -- |t Other SnAr Substitution Pathways. |
| 520 | |a This book provides a comprehensive overview of nucleophilic aromatic substitutions, focusing on the mechanistic and synthetic features that govern these reactions. The first chapter presents a detailed mechanistic analysis of the factors determining the feasibility of SNAr substitutions, providing decisive information to predict regioselectivity of many reactions and to define the conditions for concerted SNAr processes. Reflecting the key role played by these species as intermediates in most SNAr reactions, chapter 2 then discusses the chemistry of anionic sigma-complexes. | ||
| 588 | 0 | |a Online resource; title from home page (Wiley, viewed May 14, 2014). | |
| 546 | |a English. | ||
| 590 | |a ProQuest Ebook Central |b Ebook Central Academic Complete | ||
| 650 | 0 | |a Aromatic compounds |x Synthesis. | |
| 650 | 0 | |a Substitution reactions. | |
| 650 | 0 | |a Aromatic compounds. | |
| 650 | 6 | |a Réactions de substitution. | |
| 650 | 6 | |a Composés aromatiques. | |
| 650 | 6 | |a Composés aromatiques |x Synthèse. | |
| 650 | 7 | |a SCIENCE |x Chemistry |x Organic. |2 bisacsh | |
| 650 | 7 | |a Substitution reactions |2 fast | |
| 650 | 7 | |a Aromatic compounds |2 fast | |
| 650 | 7 | |a Aromatic compounds |x Synthesis |2 fast | |
| 758 | |i has work: |a Modern nucleophilic aromatic substitution (Text) |1 https://id.oclc.org/worldcat/entity/E39PCGGBCfjXYPgGYq3xGRpdPP |4 https://id.oclc.org/worldcat/ontology/hasWork | ||
| 776 | 0 | 8 | |i Print version: |a Terrier, François. |t Modern nucleophilic aromatic substitution. |d Weinheim, Germany : Wiley-Vch, ©2013 |z 3527318615 |w (OCoLC)823380608 |
| 856 | 4 | 0 | |u https://ebookcentral.uam.elogim.com/lib/uam-ebooks/detail.action?docID=1204074 |z Texto completo |
| 880 | 0 | 0 | |6 505-01/(S |g Machine-generated contents note: |g 1.1. |t Introduction -- |g 1.2. |t Activation of the Aromatic System: Driving Force for SNAr Reactions -- |g 1.2.1. |t Benzene and Related Arene Derivatives -- |g 1.2.2. |t Pyridine and Related Aza-aromatics -- |g 1.2.3. |t Five-Membered Ring Heterocycles -- |g 1.2.4. |t Activation by Electron-Withdrawing Heterocyclic Units: The Superelectrophilic Dimension in SNAr Substitutions -- |g 1.3. |t Leaving Group, Nucleophile, Solvent, and Medium Effects -- |g 1.3.1. |t The Influence of the Leaving Group -- |g 1.3.1.1. |t Halogen Nucleofugality -- |g 1.3.1.2. |t The Mobility of the Nitro Group and Other Leaving Groups -- |g 1.3.2. |t The Influence of the Nucleophile -- |g 1.3.2.1. |t Basicity and Polarizability -- |g 1.3.2.2. |t Ritchie and Mayr's Scales -- |g 1.3.3. |t The Influence of the Solvent -- |g 1.3.3.1. |t SNAr Reactions Involving Anionic Nucleophiles -- |g 1.3.3.2. |t SNAr Reactions Involving Neutral Nucleophiles -- |g 1.4. |t Effects of Specific Structural Variations in the Activated Ring -- |g 1.4.1. |t Ortho versus Para Activation: Hydrogen Bonding and Built-in Solvation -- |g 1.4.2. |t Reactivity at Unsubstituted versus Substituted Ring Carbon Atoms: Side Processes -- |g 1.5. |t Spectral Evidence for the Intermediacy of σμκνιδτδπ ζλ ΠΛΑο Οδαϐϟζμλπ |g 1.6. |t Base Catalysis in SNAr Reactions -- |g 1.6.1. |t The Specific Base-General Acid Mechanism -- |g 1.6.2. |t The Rate-Limiting Proton-Transfer Mechanism -- |g 1.7. |t Regioselectivity in SNAr Reactions -- |g 1.8. |t Asymmetric SNAr Substitutions -- |g 1.9. |t Concerted SNAr Substitutions -- |g 1.9.1. |t Ring Activation and Feasibility of Concerted Substitutions -- |g 1.9.2. |t Concerted Substitutions in Triazines -- |g 1.10. |t Conclusion -- |t References -- |g 2.1. |t Introduction -- |g 2.2. |t Structural Features of a-Complexes -- |g 2.2.1. |t X-Ray Crystallography -- |g 2.2.2. |t Gas-Phase Meisenheimer Complexes -- |g 2.2.3. |t NMR Spectroscopy -- |g 2.2.3.1. |t Complexation at Unsubstituted Carbons -- |g 2.2.3.2. |t Complexation at Substituted Carbons -- |g 2.2.3.3. |t Complexation versus Proton Abstraction -- |g 2.3. |t Thermodynamics and Kinetics of σμκνιδτ Εμοκαϟζμλ |g 2.3.1. |t The Nature of the Aromatic System -- |g 2.3.2. |t The Effect of Ring Substituents -- |g 2.3.3. |t Nucleophilic Reactivity at Substituted versus Unsubstituted Carbons: Steric Effects -- |g 2.3.3.1. |t Relative Reactivities and Stabilities of 1-Substituted and 1,1-Disubstituted Complexes -- |g 2.3.3.2. |t Isomeric Addition at Substituted and Unsubstituted Carbons of Electron-Deficient Aromatics: Relevance to Nucleophilic Aromatic Substitution Processes -- |g 2.3.4. |t Intramolecular Additions: Spiro Complexes -- |g 2.3.5. |t Diadduct Formation: Meta Bridging -- |g 2.3.6. |t The Effect of the Nucleophile -- |g 2.3.7. |t Solvent and Medium Effects -- |t References -- |g 3.1. |t Introduction -- |g 3.2. |t The Classical Domain of SNAr and Anionic σμκνιδταϟζμλ Οδαϐϟζσζϟυ |g 3.3. |t Reaching the Superelectrophilic Dimension -- |g 3.3.1. |t The Reference Water Reaction -- |g 3.3.2. |t σμκνιδταϟζμλ ςζϟϝ δαθ αοβμλ Λρϐιδμνϝζιδπ |g 3.3.3. |t From the pKaH2O Scale to Mayr's Electrophilicity (E) Scale -- |g 3.3.4. |t Oxidation Potentials as Descriptors of the Superelectrophilic Dimension -- |g 3.4. |t The Synthetic Potential of σμκνιδταϟζμλ αλγ ΠΛΑο Οδαϐϟζσζϟυ ζλ ϟϝδ Πρνδοδιδϐϟομνϝζιζϐ Γζκδλπζμλ |g 3.4.1. |t σμκνιδταϟζμλ Οδαϐϟζσζϟυ |g 3.4.2. |t The Synthetic Potential of SNAr Substitutions: Normal (PiCl, NBD-Cl) versus Super (DNBF-Cl, DNBZ-Cl) Electrophiles -- |g 3.5. |t Origin of the Superelectrophilicity of Neutral Heteroaromatics -- |t References -- |g 4.1. |t Introduction -- |g 4.2. |t Intermolecular Displacements of a Nitro Group -- |g 4.2.1. |t p-, o-, and m-Dinitrobenzenes- Related Substrates -- |g 4.2.2. |t Mononitro-Substituted Benzenes and Heteroarenes -- |g 4.2.3. |t Dinitro- and Trinitro-Substituted Benzenes and Related Derivatives -- |g 4.3. |t Intermolecular Displacements of Halogen and Other Leaving Groups -- |g 4.3.1. |t The Effect of the Leaving Group-Synthetic Implications -- |g 4.3.2. |t SNAr Couplings with Monoactivated Arenes -- |g 4.3.3. |t SNAr Couplings with Polyhaloaromatics -- |g 4.3.4. |t SNAr Couplings with Strongly-Activated Arenes -- |g 4.3.5. |t SNAr Couplings with Aza and Polyaza Heteroaromatics -- |g 4.4. |t Conclusion -- |t References -- |g 5.1. |t Introduction -- |g 5.2. |t SNAr Cyclizations -- |g 5.2.1. |t Substitutions with Oxygen Nucleophiles -- |g 5.2.2. |t Substitutions with Nitrogen Nucleophiles -- |g 5.2.3. |t Substitutions by Sulphur Nucleophiles -- |g 5.2.4. |t Substitutions by Carbon Nucleophiles -- |g 5.2.5. |t Intramolecular SNAr Reactions in Macrocyclization -- |g 5.3. |t Smiles Rearrangements -- |g 5.3.1. |t O -> N and N -> O Rearrangements -- |g 5.3.2. |t N -> N Rearrangements -- |g 5.3.3. |t O -> O Rearrangements -- |g 5.3.4. |t N -> S and S -> N Rearrangements -- |g 5.3.5. |t S -> O and Se -> O Rearrangements -- |g 5.3.6. |t Rearrangements with C-C Bond Formation. Truce-Smiles Rearrangements -- |g 5.4. |t Conclusion -- |t References -- |g 6.1. |t Introduction -- |g 6.2. |t Reactions Involving Oxidation of σμκνιδτϞυνδ Ζλϟδοκδγζαϟδπ |g 6.2.1. |t Spontaneous Oxidations -- |g 6.2.2. |t Reactions Involving an External Oxidizing Agent (ONSH) -- |g 6.2.2.1. |t Oxidation of Oxygen- and Nitrogen-Bonded Adducts -- |g 6.2.2.2. |t Oxidation of Carbon-Based aH Adducts -- |g 6.2.2.3. |t Electrochemical Oxidation -- |g 6.3. |t Vicarious Nucleophilic Aromatic Substitutions of Hydrogen (VNS) -- |g 6.3.1. |t VNS Amination and Hydroxylation Processes -- |g 6.3.2. |t VNS Substitutions with Carbon Nucleophiles -- |g 6.3.2.1. |t Effect of the Structure of the Nitroarene -- |g 6.3.2.2. |t Effect of the Structure of the Carbanion -- |g 6.4. |t Deoxygenative SNArH Substitutions -- |g 6.5. |t Cine and Tele Substitutions -- |g 6.5.1. |t The Von Richter Rearrangement -- |g 6.5.2. |t o-Dinitro Six-Membered Ring Aromatics and Related Derivatives -- |g 6.5.3. |t m-Diactivated Arenes and Related Substrates -- |g 6.5.4. |t Cine and Tele Substitutions in Heterocyclic Series -- |g 6.5.4.1. |t Aza and Polyaza aromatics -- |g 6.5.4.2. |t Five-Membered Ring Heteroaromatics -- |g 6.6. |t Conclusion -- |t References -- |g 7.1. |t SN(ANRORC) Substitutions -- |g 7.1.1. |t Introduction -- |g 7.1.2. |t Aza Aromatics without Nitro Activation -- |g 7.1.3. |t Nitro-Activated Aza Aromatics -- |g 7.1.4. |t Conclusion -- |g 7.2. |t Radical Nucleophilic Aromatic Substitutions -- |g 7.2.1. |t Introduction -- |g 7.2.2. |t Radical Anion Formation in "SNAr" Systems -- |g 7.2.3. |t Representative Radical Nucleophilic Aromatic Substitutions -- |g 7.2.4. |t Substitutions via Charge-Transfer Complexes of Anionic Radical Character -- |g 7.3. |t Nucleophilic Aromatic Photosubstitutions -- |g 7.3.1. |t General Features -- |g 7.3.2. |t SN2Ar* Reactions -- |g 7.3.3. |t SN(ET)Ar* Reactions -- |g 7.3.4. |t SN1Ar* Reactions -- |g 7.3.5. |t Regioselectivity and Chemical Theory -- |g 7.3.5.1. |t The Frontier Molecular Orbital Theory -- |g 7.3.5.2. |t The "Energy Gap" Model and Other Recent Approaches -- |t References. |
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