Comprehensive Organic Reactions in Aqueous Media, 2nd Edition

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.