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Categories: Organic Chemistry >> Synthesis >> Solvents

Comprehensive Organic Reactions in Aqueous Media

Chao-Jun Li, Tak-Hang Chan

Hardcover, 417 Pages
2nd Edition, June 2007
ISBN: 978-0-471-76129-7
Wiley

Description

An extensive update of the classic reference on organic reactions in water

Published almost a decade ago, the first edition has served as the guide for research in this burgeoning field. Due to the cost, safety, efficiency, and environmental friendliness of water as a solvent, there are many new applications in industry and academic laboratories. More than forty percent of this extensively updated second edition covers new reactions. For ease of reference, it is organized by functional groups. A core reference, Comprehensive Organic Reactions in Aqueous Media, Second Edition:

* Provides the most comprehensive coverage of aqueous organicreactions available
* Covers the basic principles and theory and progresses to applications
* Includes alkanes, alkenes, aromatics, electrophilic substitutions, carbonyls, alpha, beta-unsaturated carbonyls, carbon-nitrogen bonds, organic halides, pericyclic reactions, photochemical reactions, click chemistry, and multi-step syntheses?
* Provides examples of applications in industry

This is the premier reference for chemists and chemical engineers in industry or research, as well as for students in advanced-level courses.

Editorial Review

The methods of green chemistry continue to grow in importance. Alternative processes help to conserve resources and can even reduce costs. The replacement of convention solvents with water, which is harmless to health and is available in large quantities, is one of the most interesting basic approaches along these lines.

"Comprehensive Organic Reactions in Aqueous Media" presents the solvent properties of water in detail. Next, the text describes reactions that have previously been optimized for this solvent, organized by functional group. In each chapter, the authors have succeeded in precisely sketching out the potential. The introductions are easy to understand, and clarify the essential features of the solvent with respect to the reactions being described. Examples from the current literature have been carefully selected, and cover a broad range of transformations. This makes the book quite useful, and provides the reader with an overview of the available options and the state of the art. The multitude of citations to the broader literature make "Comprehensive Organic Reactions in Aqueous Media" a very good resource for consultation.

Advanced students and research and development chemists with an interest in green chemistry are highly recommended to purchase this book. The reader will encounter interesting details in a number of passages in this work, which always clearly indicate the use of water as a strongly recommended solvent for specific reactions. To mention one example, when run in an aqueous medium, some Diels-Alder reactions exhibit rate accelerations of several orders of magnitude.

Contents

1. INTRODUCTION.
1.1 The Structure and Forms of Water.
1.2 Properties of Water.
1.3 Solvation.
1.4 Hydrophobic Effect.
1.5 Salt Effect.
1.6 Water Under Extreme Conditions
References.

2. ALKANES.
2.1 Oxygenation of Alkanes.
2.2 Halogenation of Alkanes.
2.3 Formation of Carbon–Carbon Bonds.
2.4 D/H Exchange of Alkanes in Water.
References.

3. ALKENES.
3.1 Reduction.
3.2 Electrophilic Additions.
3.3 Radical Reactions of Alkenes.
3.4 Carbene Reactions.
3.5 Alkene Isomerization.
3.6 Transition-Metal Catalyzed C–C Formation Reactions.
3.7 Olefin Metathesis.
3.8 Reaction of Allylic C–H Bond.

4. ALKYNES.
4.1 Reaction of Terminal Alkynes.
4.2 Additions of C≡C bonds.
4.3 Transition-Metal Catalyzed Cycloadditions.
4.4 Other Reactions.
References.

5. ALCOHOLS, PHENOLS, ETHERS, THIOLS, AND THIOETHERS.
5.1 Oxidation of Alcohols.
5.2 Substitutions/Elimination.
5.3 Addition of Alcohols, Phenols, and Thiols to Alkene and Alkyne Bonds.
5.4 Addition of Alcohols to C=O Bonds: Esterification and Acetal Formations.
5.5 Reaction of Ethers and Cyclic Ethers.
5.6 Reaction of Sulfur Compounds.

6. ORGANIC HALIDES.
6.1 General.
6.2 Reduction.
6.3 Elimination Reactions.
6.4 Nucleophilic Substitutions.
6.5 Reductive Coupling.
6.6 Carbonylation of Organic Halides.
6.7 Transition-Metal Catalyzed Coupling Reactions.
References.

7. AROMATIC COMPOUNDS.
7.1 General.
7.2 Substitution Reactions.
7.3 Oxidation Reactions.
7.4 Reductions.
References.

8. ALDEHDYE AND KETONES.
8.1 Reduction.
8.2 Oxidation.
8.3 Nucleophilic Addition: C–C Bond Formation.
8.4 Pinacol Coupling.
8.5 Other Reactions (Halogenation and Oxidation of α-H).
References.

9. CARBOXYLIC ACIDS AND DERIVATIVES.
9.1 General.
9.2 Carboxylic Acids.
9.3 Carboxylic Acid Derivatives.
References.

10. CONJUGATED CARBONYL COMPOUNDS.
10.1 Reduction.
10.2 Epoxidation, Dihydroxylation, Hydroxyamination.
10.3 Conjugate Addition: Heteroatom.
10.4 C–C Bond Formation.
10.5 Other Reactions.
References.

11. NITROGEN COMPOUNDS.
11.1 Amines.
11.2 Imines.
11.3 Diazo Compounds.
11.4 Azides.
11.5 Nitro Compounds.
References.

12. PERICYCLIC REACTIONS.
12.1 Introduction.
12.2 Diels-Alder Reactions.
12.3 Sigmatropic Rearrangements.
12.4 Photochemical Cycloaddition Reactions.
References.

INDEX.