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Microwaves in Organic Synthesis, 2 Volume Set, 3rd Edition

Microwaves in Organic Synthesis, 2 Volume Set, 3rd Edition

Antonio de la Hoz (Editor), André Loupy (Editor)

ISBN: 978-3-527-33116-1

Jan 2013

1303 pages

Description

The third edition of the bestselling two-volume reference covers everything you need to know about microwave technology for synthesis
- from the best equipment to nonthermal effects, from solid-support reactions to catalysis. Completely revised and updated with half of the authors completely new to the project, this comprehensive work is clearly divided into two parts on the fundamentals of microwave irradiation, and application of microwaves and synergies with other enabling techniques. Also new to this edition are chapters on on-line monitoring, flow chemistry, combination with ultrasounds and natural products, including multicomponent reactions.

An indispensable source for organic, catalytic, physical, and medicinal chemists.
Contents to Volume 1

PREFACE

PART I: Fundamental Aspects of Microwave Irradiation in Organic Chemistry

MICROWAVE -
MATERIALS INTERACTIONS AND DIELECTRIC PROPERTIES: FROM MOLECULES AND MACROMOLECULES TO SOLIDS AND COLLOIDAL SUSPENSIONS
Fundamentals of Microwave -
Matter Interactions
Dielectric Properties and Molecular Behavior
Conclusion

DEVELOPMENT AND DESIGN OF REACTORS IN MICROWAVE-ASSISTED CHEMISTRY
Introduction
Basic Concepts for Reactions and Reactors in Organic Synthesis
Methods for Enhancing the Rates of Organic Reactions
Microwave-Assisted Organic Syntheses
Commercial Microwave Reactors
Selected Equipment and Applications
Qualification and Validation of Reactors and Results
Conclusion and the Future

KEY INGREDIENTS FOR MASTERY OF CHEMICAL MICROWAVE PROCESSES
The Systemic Approach
Thermal Dependence of Dielectric Loss
Electric Field Effects
Loop Modes or Strange Solutions of Maxwell's Equations
Hydrodynamic Aspects
Thermodynamic and Other Effects of Electric Fields
Athermal and Specific Effects of Electric Field
The Thermal Path Effect: Anisothermal Conditions
Hot Spots and Heterogeneous Kinetics
Conclusion

NONTHERMAL EFFECTS OF MICROWAVES IN ORGANIC SYNTHESIS
Introduction
Origin of Microwave Effects
Specific Nonthermal Microwave Effects
Effects of the Medium
Effects Depending on Reaction Mechanisms
Effects Depending on the Position of the Transition State Along the Reaction coordinate
Effects on Selectivity
Some Illustrative Examples
Concerning the Absence of Microwave Effects
Conclusion: Suitable Conditions for Observation of Specific MW Effects

SELECTIVITY MODIFICATIONS UNDER MICROWAVE IRRADIATION
Introduction
Selective Heating
Modification of Chemoselectivity and Regioselectivity
Modification of Stereo- and Enantioselectivity
Conclusion

ELUCIDATION OF MICROWAVE EFFECTS: METHODS, THEORIES, AND PREDICTIVE MODELS
Introduction
Thermal Effects
Non-Thermal Effects
Conclusion

MICROWAVE SUSCEPTORS
Introduction
Graphite as a Sensitizer
Graphite as Sensitizer and Catalyst
The Use of Silicon Carbide Susceptors in Microwave Chemistry

TOOLS FOR MONITORING REACTIONS PERFORMED USING MICROWAVE HEATING
Introduction
Watching Microwave-Heated Reactions in Real Time
Monitoring Microwave-Heated Reactions Using InSitu Spectroscopic Tools
Conclusion

MICROWAVE FREQUENCY EFFECTS IN ORGANIC SYNTHESIS
Introduction
Historical Review of Microwave Frequency Effects in Chemical Reactions
Microwave Chemical Reaction Apparatus Operating at Various Frequencies
Frequency Effects and Heating Efficiency in Various Solutions
Examples of Chemical Reactions Impacted by Microwave Frequency Effects
Conclusion

PART II: Applications of Microwave Irradiation

ORGANIC SYNTHESIS USING MICROWAVES AND SUPPORTED REAGENTS
Introduction
Microwave-Accelerated Solvent-Free Organic Reactions
Protection -
Deprotection Reactions
Condensation Reactions
Isomerization and Rearrangement Reactions
Diels -
Alder Cycloaddition of a Triazole Ring
Addition Reactions
Oxidation Reactions - Oxidation of Alcohols and Sulfides
Reduction Reactions
Synthesis of Heterocyclic Compounds
Miscellaneous Reactions
Conclusion

GASEOUS REACTANTS IN MICROWAVE-ASSISTED SYNTHESIS
Introduction
Liquid-Phase Synthesis
Wet Air Oxidation
Gas-Phase Synthesis
Waste Gas Treatment
Conclusion and Outlook

MICROWAVES AND ELECTROCHEMISTRY
Introduction to Microwave Assisted Electrode Processes
Macroelectrode Processes in the Presence of Microwaves
Microelectrode Processes in the Presence of Microwaves
Junction-Electrode Processes in the Presence of Microwaves
Electrochemical Flow Reactor Processes in the Presence of Microwaves
Future Trends

THE COMBINED USE OF MICROWAVES AND ULTRASOUND: METHODS AND PRACTICE
Introduction
The Search for the Best Coupling
Microwave- and Ultrasound-Enhanced Synthesis and Catalysis
Formation of Advanced Materials
Conclusion and Future Trends

MICROWAVES IN PHOTOCHEMISTRY AND PHOTOCATALYSIS
Introduction
UV/Vis Discharges in Electrodeless Lamps
Microwave Photochemical and Photocatalytic Reactors
Interactions of UV/Vis and Microwave Radiation with Matter
Microwave Photochemistry and Photocatalysis
Applications
Future Trends

Contents to Volume 2

PREFACE

MICROWAVE-HEATED TRANSITION METAL-CATALYZED COUPLING REACTIONS
Introduction
Cross-Coupling Reactions
Arylation of C, N, O, S, P and Halogen Nucleophiles
The Heck Reaction
Carbonylative Coupling Reactions
Conclusion

MICROWAVES IN HETEROCYCLIC CHEMISTRY
Introduction
Microwave-Assisted Synthesis of Four- and Five-Membered Systems with One and More Than Two Heteroatoms
Six-Membered Systems with One Heteroatom
Six-Membered Systems with More Than One Heteroatom
Bicyclic Systems (Six Atoms + Five Atoms) with One, Two, and More Heteroatoms
Bicyclic Systems (Six Atoms + Six Atoms) with One, Two, and More Heteroatoms
Seven Membered Heterocycles with Two Heteroatoms: Microwave-Assisted Synthesis of Benzodiazepines and Related Compounds
Microwave-Assisted Nucleophilic Aromatic Substitution (SNAr)
Microwaves in Total Synthesis of Bioactive Heterocycles
Conclusion

MICROWAVE-ASSISTED CYCLOADDITION REACTIONS
Introduction
Microwave-Assisted [3 + 2]-Cycloaddition Reactions
Microwave-Assisted [4 + 2]-Cycloaddition Reactions
Microwave-Assisted [2 + 2]-Cycloaddition Reactions
Other Microwave-Assisted Cycloaddition Reactions
Conclusion

MICROWAVE-ASSISTED HETEROGENEOUSLY CATALYZED PROCESSES
Introduction
Acid-Catalyzed Reactions
Based-Catalyzed Reactions
Redox Reactions
Coupling Reactions
Other Reactions
Conclusion and Outlook

MICROWAVES IN THE SYNTHESIS OF NATURAL PRODUCTS
Introduction
Total Synthesis of Various Classes of Natural Products
Total Synthesis of Various Classes of Alkaloids
Synthesis of Analogs of Natural Products
Synthesis of Building Blocks (Subunits) for Natural Product
Conclusion and Overview

MICROWAVE-ENHANCED SYNTHESIS OF PEPTIDES, PROTEINS, AND PEPTIDOMIMETICS
Introduction
Synthesis Approaches
Microwave Theory for Peptide Synthesis
Na-Amino Protection Strategies
Amide Bond Formation
Modified Peptides
Non-Natural Peptidomimetics
Resin Cleavage
Recommended Protocols
Conclusion
Abbreviations

A JOURNEY INTO RECENT MICROWAVE-ASSISTED CARBOHYDRATE CHEMISTRY
Introduction
Acylation
Glycosylation
Halogenation-Dehalogenation
Sulfation
Anomerization
Synthesis of Sugar Derivatives
Synthesis of Biologically and Pharmacological Active Compounds
Synthesis of Heterocycles
Synthesis of Phosphorus Compounds
Synthesis of Nanostructured Materials
Conclusion

POLYMER CHEMISTRY UNDER MICROWAVE IRRADIATION
Introduction
Synthesis of Polymers Under Microwave Irradiation
Conclusion

APPLICATION OF MICROWAVE IRRADIATION IN CARBON NANOSTRUCTURES
Fullerenes Under Microwave Irradiation
Microwave Irradiation in Carbon Nanotubes
Microwave Irradiation in Other Carbon Nanoforms
Conclusion

MICROWAVE-ASSISTED MULTICOMPONENT REACTIONS IN THE SYNTHESIS OF HETEROCYCLES
Introduction
Nitrogen Heterocycles
Oxygen-Containing Rings
Sulfur-Containing Rings
Oxygen- and Nitrogen-Containing Rings
Carbacycles
Multiple Ring Systems
Conclusion
Abbreviations

MICROWAVE-ASSISTED CONTINUOUS FLOW ORGANIC SYNTHESIS (MACOS)
Introduction
Equipment
MACOS in Homogeneous System
MACOS in Heterogeneous System
Conclusion and Outlook

INDEX