Modern Nucleophilic Aromatic Substitution (eBook, PDF)
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Modern Nucleophilic Aromatic Substitution (1673)
DE NW EB DLISBN: 9783527656172 bzw. 3527656170, in Deutsch, Wiley-VCH, neu, E-Book, elektronischer Download.
Lieferung aus: Deutschland, Versandkostenfrei.
Modern Nucleophilic Aromatic Substitution: InhaltsangabePreface XI1 The SNAr Reactions: Mechanistic Aspects 11.1 Introduction 11.2 Activation of the Aromatic System: Driving Force for SNAr Reactions 51.2.1 Benzene and Related Arene Derivatives 51.2.2 Pyridine and Related Aza-aromatics 111.2.3 Five-Membered Ring Heterocycles 151.2.4 Activation by Electron-Withdrawing Heterocyclic Units: The Superelectrophilic Dimension in SNAr Substitutions 181.3 Leaving Group, Nucleophile, Solvent, and Medium Effects 241.3.1 The Influence of the Leaving Group 241.3.1.1 Halogen Nucleofugality 241.3.1.2 The Mobility of the Nitro Group and Other Leaving Groups 281.3.2 The Influence of the Nucleophile 311.3.2.1 Basicity and Polarizability 311.3.2.2 Ritchie and Mayr&rsquo s Scales 361.3.3 The Influence of the Solvent 381.3.3.1 SNAr Reactions Involving Anionic Nucleophiles 381.3.3.2 SNAr Reactions Involving Neutral Nucleophiles 421.4 Effects of Specific Structural Variations in the Activated Ring 461.4.1 ortho versus para Activation: Hydrogen Bonding and Built-in Solvation 461.4.2 Reactivity at Unsubstituted versus Substituted Ring Carbon Atoms: Side Processes 501.5 Spectral Evidence for the Intermediacy of &sigma -Complexes in SNAr Reactions 521.6 Base Catalysis in SNAr Reactions 571.6.1 The Specific Base&ndash General Acid Mechanism 611.6.2 The Rate-Limiting Proton-Transfer Mechanism 651.7 Regioselectivity in SNAr Reactions 681.8 Asymmetric SNAr Substitutions 731.9 Concerted SNAr Substitutions 761.9.1 Ring Activation and Feasibility of Concerted Substitutions 761.9.2 Concerted Substitutions in Triazines 791.10 Conclusion 83References 842 Structure and Reactivity of Anionic &sigma -Complexes 952.1 Introduction 952.2 Structural Features of &sigma -Complexes 962.2.1 X-Ray Crystallography 962.2.2 Gas-Phase Meisenheimer Complexes 1002.2.3 NMR Spectroscopy 1032.2.3.1 Complexation at Unsubstituted Carbons 1032.2.3.2 Complexation at Substituted Carbons 1142.2.3.3 Complexation versus Proton Abstraction 1232.3 Thermodynamics and Kinetics of &sigma -Complex Formation 1252.3.1 The Nature of the Aromatic System 1262.3.2 The Effect of Ring Substituents 1292.3.3 Nucleophilic Reactivity at Substituted versus Unsubstituted Carbons: Steric Effects 1352.3.3.1 Relative Reactivities and Stabilities of 1-Substituted and 1,1-Disubstituted Complexes 1352.3.3.2 Isomeric Addition at Substituted and Unsubstituted Carbons of Electron-Deficient Aromatics: Relevance to Nucleophilic Aromatic Substitution Processes 1402.3.4 Intramolecular Additions: Spiro Complexes 1452.3.5 Diadduct Formation: Meta Bridging 1482.3.6 The Effect of the Nucleophile 1502.3.7 Solvent and Medium Effects 152References 1563 The Superelectrophilic Dimension in SNAr and Related &sigma -Complexation Processes 1633.1 Introduction 1633.2 The Classical Domain of SNAr and Anionic &sigma -Complexation Reactivity 1643.3 Reaching the Superelectrophilic Dimension 1673.3.1 The Reference Water Reacti Benzenes and Heteroarenes 2164.2.3 Dinitro- and Trinitro-Substituted Benzenes and Related Derivatives 2284.3 Intermolecular Displacements of Halogen and Other Leaving Groups 2364.3.1 The Effect of the Leaving Group &ndash Synthetic Implications 2364.3.2 SNAr Couplings with Monoactivated Arenes 2424.3.3 SNAr Couplings with Polyhaloaromatics 2514.3.4 SNAr Couplings with Strongly Activated Arenes 2554.3.5 SNAr Couplings with Aza and Polyaza Heteroaromatics 2634.4 Conclusion 269References 2715 Intramolecular SNAr Reactions 2795.1 Introduction 2795.2 SNAr Cyclizations 2805.2.1 Substitutions with Oxygen Nucleophiles 2805.2.2 Substitutions with Nitrogen Nucleophiles 2905.2.3 Substitutions by Sulfur Nucleophiles 2965.2.4 Substitutions by Carbon Nucleophiles 2985.2.5 Intramolecular SNAr Reactions in Macrocyclization 3005.3 Smiles Rearrangements 3035.3.1 O&rarr N and N&rarr O Rearrangements 3045.3.2 N&rarr N Rearrangements 3115.3.3 O&rarr O Rearrangements 3155.3.4 N&rarr S and S&rarr N Rearrangements 3185.3.5 S&rarr O and Se&rarr O Rearrangements 3215.3.6 Rearrangements with C&ndash C Bond Formation. Truce&ndash Smiles Rearrangements 3255.4 Conclusion 331References 3326 Nucleophilic Aromatic Substitutions of Hydrogen 3376.1 Introduction 3376.2 Reactions Involving Oxidation of &sigma -Complex-Type Intermediates 3396.2.1 Spontaneous Oxidations 3396.2.2 Reactions Involving an External Oxidizing Agent (ONSH) 3516.2.2.1 Oxidation of Oxygen- and Nitrogen-Bonded Adducts 3536.2.2.2 Oxidation of Carbon-Based &sigma H Adducts 3576.2.2.3 Electrochemical Oxidation 3726.3 Vicarious Nucleophilic Aromatic Substitutions of Hydrogen (VNS) 3746.3.1 VNS Amination and Hydroxylation Processes 3746.3.2 VNS Substitutions with Carbon Nucleophiles 3786.3.2.1 Effect of the Structure of the Nitroarene 3796.3.2.2 Effect of the Structure of the Carbanion 3846.4 Deoxygenative SNArH Substitutions 3956.5 Cine and Tele Substitutions 3976.5.1 The Von Richter Rearrangement 3986.5.2 o-Dinitro Six-Membered Ring Aromatics and Related Derivatives 4006.5.3 m-Diactivated Arenes and Related Substrates 4046.5.4 Cine and Tele Substitutions in Heterocyclic Series 4076.5.4.1 Aza and Polyaza aromatics 4076.5.4.2 Five-Membered Ring Heteroaromatics 4096.6 Conclusion 414References 4157 Other SNAr Substitution Pathways 4237.1 SN(ANRORC) Substitutions 4237.1.1 Introduction 4237.1.2 Aza Aromatics without Nitro Activation 4237.1.3 Nitro-Activated Aza Aromatics 4267.1.4 Conclusion 4297.2 Radical Nucleophilic Aromatic Substitutions 4307.2.1 Introduction 4307.2.2 Radical Anion Formation in &lsquo &lsquo SNAr&rsquo &rsquo Systems 4317.2.3 Representative Radical Nucleophilic Aromatic Substitutions 4387.2.4 Substitutions via Charge-Transfer Complexes of Anionic Radical Character 4457.3 Nucleophilic Aromatic Photosubstitutions 44, Englisch, Ebook.
Modern Nucleophilic Aromatic Substitution: InhaltsangabePreface XI1 The SNAr Reactions: Mechanistic Aspects 11.1 Introduction 11.2 Activation of the Aromatic System: Driving Force for SNAr Reactions 51.2.1 Benzene and Related Arene Derivatives 51.2.2 Pyridine and Related Aza-aromatics 111.2.3 Five-Membered Ring Heterocycles 151.2.4 Activation by Electron-Withdrawing Heterocyclic Units: The Superelectrophilic Dimension in SNAr Substitutions 181.3 Leaving Group, Nucleophile, Solvent, and Medium Effects 241.3.1 The Influence of the Leaving Group 241.3.1.1 Halogen Nucleofugality 241.3.1.2 The Mobility of the Nitro Group and Other Leaving Groups 281.3.2 The Influence of the Nucleophile 311.3.2.1 Basicity and Polarizability 311.3.2.2 Ritchie and Mayr&rsquo s Scales 361.3.3 The Influence of the Solvent 381.3.3.1 SNAr Reactions Involving Anionic Nucleophiles 381.3.3.2 SNAr Reactions Involving Neutral Nucleophiles 421.4 Effects of Specific Structural Variations in the Activated Ring 461.4.1 ortho versus para Activation: Hydrogen Bonding and Built-in Solvation 461.4.2 Reactivity at Unsubstituted versus Substituted Ring Carbon Atoms: Side Processes 501.5 Spectral Evidence for the Intermediacy of &sigma -Complexes in SNAr Reactions 521.6 Base Catalysis in SNAr Reactions 571.6.1 The Specific Base&ndash General Acid Mechanism 611.6.2 The Rate-Limiting Proton-Transfer Mechanism 651.7 Regioselectivity in SNAr Reactions 681.8 Asymmetric SNAr Substitutions 731.9 Concerted SNAr Substitutions 761.9.1 Ring Activation and Feasibility of Concerted Substitutions 761.9.2 Concerted Substitutions in Triazines 791.10 Conclusion 83References 842 Structure and Reactivity of Anionic &sigma -Complexes 952.1 Introduction 952.2 Structural Features of &sigma -Complexes 962.2.1 X-Ray Crystallography 962.2.2 Gas-Phase Meisenheimer Complexes 1002.2.3 NMR Spectroscopy 1032.2.3.1 Complexation at Unsubstituted Carbons 1032.2.3.2 Complexation at Substituted Carbons 1142.2.3.3 Complexation versus Proton Abstraction 1232.3 Thermodynamics and Kinetics of &sigma -Complex Formation 1252.3.1 The Nature of the Aromatic System 1262.3.2 The Effect of Ring Substituents 1292.3.3 Nucleophilic Reactivity at Substituted versus Unsubstituted Carbons: Steric Effects 1352.3.3.1 Relative Reactivities and Stabilities of 1-Substituted and 1,1-Disubstituted Complexes 1352.3.3.2 Isomeric Addition at Substituted and Unsubstituted Carbons of Electron-Deficient Aromatics: Relevance to Nucleophilic Aromatic Substitution Processes 1402.3.4 Intramolecular Additions: Spiro Complexes 1452.3.5 Diadduct Formation: Meta Bridging 1482.3.6 The Effect of the Nucleophile 1502.3.7 Solvent and Medium Effects 152References 1563 The Superelectrophilic Dimension in SNAr and Related &sigma -Complexation Processes 1633.1 Introduction 1633.2 The Classical Domain of SNAr and Anionic &sigma -Complexation Reactivity 1643.3 Reaching the Superelectrophilic Dimension 1673.3.1 The Reference Water Reacti Benzenes and Heteroarenes 2164.2.3 Dinitro- and Trinitro-Substituted Benzenes and Related Derivatives 2284.3 Intermolecular Displacements of Halogen and Other Leaving Groups 2364.3.1 The Effect of the Leaving Group &ndash Synthetic Implications 2364.3.2 SNAr Couplings with Monoactivated Arenes 2424.3.3 SNAr Couplings with Polyhaloaromatics 2514.3.4 SNAr Couplings with Strongly Activated Arenes 2554.3.5 SNAr Couplings with Aza and Polyaza Heteroaromatics 2634.4 Conclusion 269References 2715 Intramolecular SNAr Reactions 2795.1 Introduction 2795.2 SNAr Cyclizations 2805.2.1 Substitutions with Oxygen Nucleophiles 2805.2.2 Substitutions with Nitrogen Nucleophiles 2905.2.3 Substitutions by Sulfur Nucleophiles 2965.2.4 Substitutions by Carbon Nucleophiles 2985.2.5 Intramolecular SNAr Reactions in Macrocyclization 3005.3 Smiles Rearrangements 3035.3.1 O&rarr N and N&rarr O Rearrangements 3045.3.2 N&rarr N Rearrangements 3115.3.3 O&rarr O Rearrangements 3155.3.4 N&rarr S and S&rarr N Rearrangements 3185.3.5 S&rarr O and Se&rarr O Rearrangements 3215.3.6 Rearrangements with C&ndash C Bond Formation. Truce&ndash Smiles Rearrangements 3255.4 Conclusion 331References 3326 Nucleophilic Aromatic Substitutions of Hydrogen 3376.1 Introduction 3376.2 Reactions Involving Oxidation of &sigma -Complex-Type Intermediates 3396.2.1 Spontaneous Oxidations 3396.2.2 Reactions Involving an External Oxidizing Agent (ONSH) 3516.2.2.1 Oxidation of Oxygen- and Nitrogen-Bonded Adducts 3536.2.2.2 Oxidation of Carbon-Based &sigma H Adducts 3576.2.2.3 Electrochemical Oxidation 3726.3 Vicarious Nucleophilic Aromatic Substitutions of Hydrogen (VNS) 3746.3.1 VNS Amination and Hydroxylation Processes 3746.3.2 VNS Substitutions with Carbon Nucleophiles 3786.3.2.1 Effect of the Structure of the Nitroarene 3796.3.2.2 Effect of the Structure of the Carbanion 3846.4 Deoxygenative SNArH Substitutions 3956.5 Cine and Tele Substitutions 3976.5.1 The Von Richter Rearrangement 3986.5.2 o-Dinitro Six-Membered Ring Aromatics and Related Derivatives 4006.5.3 m-Diactivated Arenes and Related Substrates 4046.5.4 Cine and Tele Substitutions in Heterocyclic Series 4076.5.4.1 Aza and Polyaza aromatics 4076.5.4.2 Five-Membered Ring Heteroaromatics 4096.6 Conclusion 414References 4157 Other SNAr Substitution Pathways 4237.1 SN(ANRORC) Substitutions 4237.1.1 Introduction 4237.1.2 Aza Aromatics without Nitro Activation 4237.1.3 Nitro-Activated Aza Aromatics 4267.1.4 Conclusion 4297.2 Radical Nucleophilic Aromatic Substitutions 4307.2.1 Introduction 4307.2.2 Radical Anion Formation in &lsquo &lsquo SNAr&rsquo &rsquo Systems 4317.2.3 Representative Radical Nucleophilic Aromatic Substitutions 4387.2.4 Substitutions via Charge-Transfer Complexes of Anionic Radical Character 4457.3 Nucleophilic Aromatic Photosubstitutions 44, Englisch, Ebook.
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Modern Nucleophilic Aromatic Substitution
DE NWISBN: 9783527656172 bzw. 3527656170, in Deutsch, Wiley-VCH, neu.
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Modern Nucleophilic Aromatic Substitution (2013)
DE NW EBISBN: 9783527656172 bzw. 3527656170, in Deutsch, Wiley-Vch Verlag GmbH, neu, E-Book.
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Modern Nucleophilic Aromatic Substitution (2013)
DE NW EBISBN: 9783527656172 bzw. 3527656170, in Deutsch, Wiley-Vch Verlag GmbH, neu, E-Book.
Lieferung aus: Deutschland, Sofort per Download lieferbar.
Die Beschreibung dieses Angebotes ist von geringer Qualität oder in einer Fremdsprache. Trotzdem anzeigen
Die Beschreibung dieses Angebotes ist von geringer Qualität oder in einer Fremdsprache. Trotzdem anzeigen
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Modern Nucleophilic Aromatic Substitution
EN NW EB DLISBN: 9783527656172 bzw. 3527656170, in Englisch, Springer Berlin Heidelberg, neu, E-Book, elektronischer Download.
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Modern Nucleophilic Aromatic Substitution (eBook, PDF)
DE NWISBN: 9783527656172 bzw. 3527656170, in Deutsch, Wiley-VCH, Weinheim, Deutschland, neu.
Lieferung aus: Deutschland, zzgl. Versandkosten.
Die Beschreibung dieses Angebotes ist von geringer Qualität oder in einer Fremdsprache. Trotzdem anzeigen
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