Flash Chemistry Fast Organic Synthesis in Microsystems
by Yoshida, Jun-ichiEdition: 1st
Format: Hardcover
Pub. Date: 2008-11-03
Publisher(s): Wiley
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Summary
Have you ever wished you could speed up your organic syntheses without losing control of the reaction? Flash Chemistry is a new concept which offers an integrated scheme for fast, controlled organic synthesis. It brings together the generation of highly reactive species and their reactions in microsystems to enable highly controlled organic syntheses on a preparative scale in timescales of a few seconds or less.Flash Chemistry - Fast Chemical Reactions in Microsystems is the first dedicated book to describe this exciting new technique, and is an essential introduction for anyone working in organic synthesis, process chemistry, chemical engineering and physical organic chemistry concerned with fundamental aspects of chemical reactions and synthesis and the production of organic compounds.
Author Biography
Professor Jun-ichi Yoshida, Department of Synthetic Chemistry and Biological Chemistry, Graduate School of Engineering, Kyoto University, Japan
Table of Contents
| Preface | p. xi |
| Introduction | p. 1 |
| Flask Chemistry | p. 2 |
| Flash Chemistry | p. 3 |
| Flask Chemistry or Flash Chemistry | p. 4 |
| References | p. 5 |
| The Background to Flash Chemistry | p. 7 |
| How do Chemical Reactions Take Place? | p. 7 |
| Macroscopic View of Chemical Reactions | p. 8 |
| Thermodynamic Equilibrium and Kinetics | p. 8 |
| Kinetics | p. 10 |
| Transition State Theory | p. 12 |
| Femtosecond Chemistry and Reaction Dynamics | p. 12 |
| Reactions for Dynamics and Reactions for Synthesis | p. 13 |
| Bimolecular Reactions in the Gas Phase | p. 15 |
| Bimolecular Reactions in the Solution Phase | p. 16 |
| Fast Chemical Synthesis Inspired by Reaction Dynamics | p. 17 |
| References | p. 18 |
| What is Flash Chemistry? | p. 19 |
| Why is Flash Chemistry Needed? | p. 23 |
| Chemical Reaction, an Extremely Fast Process at Molecular Level | p. 23 |
| Rapid Construction of Chemical Libraries | p. 24 |
| Rapid Synthesis of Radioactive Positron Emission Tomography Probes | p. 27 |
| On-demand Rapid Synthesis in Industry | p. 30 |
| Conclusions | p. 31 |
| References | p. 31 |
| Methods of Activating Molecules | p. 33 |
| Thermal Activation of Organic Molecules | p. 33 |
| High Temperature Reactions | p. 33 |
| Flash Vacuum Pyrolysis | p. 35 |
| Microwave Reactions | p. 36 |
| Photochemical Activation | p. 38 |
| Electrochemical Activation | p. 39 |
| Chemical Activation | p. 41 |
| Accumulation of Reactive Species | p. 43 |
| The Cation-pool Method | p. 44 |
| Continuous Generation of Reactive Species in a Flow System | p. 57 |
| Interconversion Between Reactive Species | p. 59 |
| Conclusions | p. 62 |
| References | p. 63 |
| Control of Extremely Fast Reactions | p. 69 |
| Mixing | p. 69 |
| How Does Mixing Take Place? | p. 70 |
| Molecular Diffusion and Brownian Motion | p. 72 |
| Disguised Chemical Selectivity | p. 73 |
| Lowering the Reaction Temperature | p. 76 |
| The High Dilution Method | p. 77 |
| Micromixing | p. 78 |
| Friedel-Crafts Alkylation Using an N-acyliminium Ion Pool | p. 78 |
| Micromixing as a Powerful Tool for Flash Chemistry | p. 85 |
| Disguised Chemical Selectivity in Competitive Parallel Reactions | p. 85 |
| Temperature Control | p. 87 |
| Exothermicity of Fast Reactions | p. 87 |
| Hammond's Postulate | p. 89 |
| The Friedel-Crafts Reaction | p. 90 |
| Solvent | p. 92 |
| Heat Transfer | p. 93 |
| Precise Temperature Control in Microflow Systems | p. 95 |
| Residence Time Control | p. 97 |
| The Discovery of Benzyne. The Concept of Reactive Intermediates | p. 99 |
| o-Bromophenyllithium | p. 99 |
| Conclusions | p. 102 |
| References | p. 102 |
| Microfluidic Devices and Microflow Systems | p. 105 |
| Brief History | p. 105 |
| Microflow Systems for Chemical Analysis | p. 106 |
| Microflow Systems for Chemical Synthesis | p. 107 |
| Characteristic Features of Microflow Systems | p. 108 |
| Microstructured Fluidic Devices | p. 110 |
| Microchip Reactors | p. 110 |
| Microtube Reactors | p. 112 |
| Micromixer | p. 113 |
| Passive Micromixers | p. 114 |
| Microheat Exchanger | p. 125 |
| Photochemical Microflow Reactor | p. 126 |
| Electrochemical Microflow Reactor | p. 128 |
| Catalyst-containing Microflow Reactor | p. 129 |
| Microflow Reactors for High-pressure and High-temperature Conditions | p. 131 |
| Conclusions | p. 133 |
| References | p. 133 |
| Applications of Flash Chemistry in Organic Synthesis | p. 137 |
| Highly Exothermic Reactions that are Difficult to Control in Macrobatch Reactors | p. 138 |
| Fluorination | p. 138 |
| Chlorination and Bromination | p. 139 |
| Nitration | p. 142 |
| 1,4-Addition Reactions of Amines | p. 143 |
| Halogen-magnesium Exchange Reactions | p. 143 |
| Oxidation of an Alkene with H[subscript 2]O[subscript 2]/HCO[subscript 2]H | p. 145 |
| Reactions in which a Reactive Intermediate Easily Decomposes in Macrobatch Reactors | p. 147 |
| Swern-Moffatt Oxidation | p. 147 |
| Organolithium Reactions | p. 150 |
| Reactions with Products which Easily Decompose in Macrobatch Reactors | p. 153 |
| Dehydration of an Allylic Alcohol to Give a Diene as an Unstable Product | p. 153 |
| Reactions in which Undesired By-products are Produced in the Subsequent Reactions in Macrobatch Reactors | p. 154 |
| Friedel-Crafts Reactions | p. 154 |
| Iodination of Aromatic Compounds | p. 157 |
| Reaction of Phenylmagnesium Bromide with Boronic Acid Trimethyl Ester | p. 158 |
| [4 + 2] Cycloaddition Reaction of N-acyliminium Ion with Olefin | p. 160 |
| Biphasic Azo-coupling Reactions | p. 162 |
| Reactions that can be Accelerated Using Microflow Systems | p. 163 |
| Acceleration of Reactions at High Temperatures | p. 163 |
| Acceleration of Radical Reactions Using Quickly Decomposing Radical Initiators | p. 165 |
| Acceleration by Controlled Mass Transfer | p. 166 |
| Acceleration by Microwaves | p. 167 |
| Acceleration by High-pressure and High-temperature Conditions | p. 167 |
| Conclusions | p. 169 |
| References | p. 169 |
| Polymer Synthesis Based on Flash Chemistry | p. 173 |
| Polymerization | p. 173 |
| Chain-growth Polymerization and Step-growth Polymerization | p. 174 |
| Molecular Weight and Molecular-weight Distribution | p. 176 |
| Cationic Polymerization | p. 176 |
| Conventional Cationic Polymerization | p. 176 |
| Living Cationic Polymerization | p. 178 |
| Ideal Living Cationic Polymerization | p. 180 |
| Fast Initiation and Mixing | p. 181 |
| Cation-pool Initiated Polymerization of Vinyl Ethers Using a Microflow System | p. 182 |
| Livingness of the Microflow System-controlled Cationic Polymerization | p. 184 |
| Comparison Between Conventional Living Cationic Polymerization and Microflow System-controlled Cationic Polymerization | p. 185 |
| Microflow System-controlled Cationic Polymerization Initiated by CF[subscript 3]SO[subscript 3]H | p. 187 |
| Free-radical Polymerization | p. 189 |
| Conventional Free-radical Polymerization | p. 189 |
| Living-radical Polymerization | p. 190 |
| Emulsion and Suspension Polymerization | p. 191 |
| Radical Polymerization in Microflow Systems | p. 192 |
| Simulation of Free-radical Polymerization in Microflow Systems | p. 196 |
| Conclusions | p. 197 |
| References | p. 197 |
| Industrial Applications of Flash Chemistry | p. 199 |
| Synthesis of Diarylethene as a Photochromic Compound (Micrometer-size Single-channel Reactor) | p. 201 |
| Synthesis of a Pharmaceutically Interesting Spiro Lactone Fragment of Neuropeptide Y (Millimeter-size Single-channel Reactor) | p. 206 |
| Grignard Exchange Process (Internal Numbering-up) | p. 208 |
| Radical Polymerization Process (Numbering-up) | p. 212 |
| Other Examples of Industrial Applications of Flash Chemistry | p. 218 |
| Flash Chemistry as a Powerful Means of Sustainable Chemical Synthesis | p. 219 |
| Conclusions | p. 220 |
| References | p. 221 |
| Outlook for Flash Chemistry | p. 223 |
| Index | p. 225 |
| Table of Contents provided by Ingram. All Rights Reserved. |
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