1: Basic Concepts in Phase-Transfer Catalysis.- A. Phase-Transfer-Catalyzed Reactions.- B. Basic Steps of Phase-Transfer Catalysis.- C. The PTC Reaction Rate Matrix.- D. Anion Transfer and Anion Activation.- E. Effect of Reaction Variables on Transfer and Intrinsic Rates.- F. Outline of Compounds Used as Phase-Transfer Catalysts.- 2: Phase-Transfer Catalysts: Fundamentals I.- A. Introduction.- B. Structural Factors Affecting the Distribution of Anions Between Aqueous and Organic Phases.- C. Structural Factors Affecting the Distribution of Phase-Transfer Catalyst Cations Between the Aqueous and Organic Phases.- D. Effects of the Organic Phase Polarity on the Distribution of Phase-Transfer Cation-Anion Pairs.- E. Effects of Changes in Organic Phase Polarity During Reaction.- F. Factors Affecting the Distribution of Phase-Transfer Catalyst Cation-Anion Pairs Between an Organic Phase and an Aqueous Phase Containing Hydroxide Ion.- G. Effect of Hydration of the Transferred Anion and the Effect of Inorganic Salt and/or Hydroxide Concentration in the Aqueous Phase.- 3: Phase-Transfer Catalysis: Fundamentals II.- A. Introduction.- B. Liquid-Liquid PTC.- C. Solid-Liquid PTC.- 4: Phase-Transfer Catalysts.- A. Introduction.- B. Use of Quaternary Salts as Phase-Transfer Catalysts.- C. Macrocyclic and Macrobicyclic Ligands.- D. PEGs, Tris (3,6-dioxaheptyl)amine (TDA-1), and Related Ethoxylated Compounds as Phase-Transfer Catalysts.- E. Other Soluble Polymers and Related Multifunctional Compounds as Phase-Transfer Catalysts.- F. Use of Dual PTC Catalysts or Use of Cocatalysts in Phase-Transfer Systems.- G. Catalysts for Transfer of Species Other Than Anions.- H. Separation and Recovery of Phase-Transfer Catalysts.- 5: Insoluble Phase-Transfer Catalysts.- A. Introduction.- B. PTC Catalysts Bound to Insoluble Resins.- C. Phase-Transfer Catalysts Bound to Inorganic Solid Supports.- D. PTC Catalysts Contained in a Separate Liquid Phase (Third-Liquid-Phase Catalyst).- 6: Variables in Reaction Design for Laboratory and Industrial Applications of Phase-Transfer Catalysis.- A. Choice of Catalyst.- B. Choice of Solvent.- C. Presence of Water.- D. Agitation.- E. Choice of Anion, Leaving Group, and Counteranion.- F. Choice of Base.- G. Guidelines for Exploring New PTC Applications.- 7: Phase-Transfer Catalysis Displacement Reactions with Simple Anions.- A. General Considerations.- B. Behavior of Various Anions in PTC Displacement Reactions.- 8: Phase-Transfer Catalysis Reaction with Strong Bases.- A. C-Alkylation.- B. N-Alkylation.- C. O-Alkylation-Etherification.- D. S- Alky lation-Thioetherification.- E. Dehydrohalogenation.- F. Carbene Reactions.- G. Condensation Reactions.- H. Deuterium Exchange, Isomerization, and Oxidation.- 9: Phase-Transfer Catalysis: Polymerization and Polymer Modification.- A. Introduction.- B. Polymer Synthesis.- C. Chemical Modification of Polymers.- 10: Phase-Transfer-Catalyzed Oxidations.- A. Introduction.- B. Permanganate Oxidations.- D. PTC Oxidations with Hydrogen Peroxide.- E. PTC Air or Oxygen Oxidations.- F. Oxidations by Persulfates.- H. PTC Oxidations with Nitric Acid.- I. PTC Carbon Tetrachloride/Sodium Hydroxide Oxidations.- J. PTC Oxidations with Periodate and Related Oxidizing Anions.- K. PTC Oxidations with Perborate.- L. PTC Oxidations with Ferrate and Ferricyanide.- M. PTC Oxidations with Superoxide.- N. PTC Electrochemical Oxidations.- O. PTC Oxidations with Other Oxidants.- 11: Phase-Transfer-Catalyzed Reductions.- A. Sodium Borohydride Reductions.- B. Lithium Aluminum Hydride Reductions.- C. Reductions withSodium Formate.- D. Reductions with Sulfur-Containing Anions.- E. Hydrogenation.- F. Reductions with Formaldehyde.- G. Electrochemical Reduction.- H. Photochemical Reduction.- I. Wolff-Kishner Reduction.- J. Reduction by Dodecarbonyltriiron and Related Species.- 12: Phase-Transfer Catalysis: Chiral Phase-Transfer-Catalyzed Formation of Carbon-Carbon Bonds.- A. Introduction.- B. Alkylation Reactions.- 13: Phase Transfer Catalysis-Transition Metal Cocatalyzed Reactions.- A. Introduction.- B. Carbonylation and Reactions with Carbon Monoxide.- B. PTC Reduction and Hydrogenation with Metal Cocatalysts.- C. Coupling Reactions of Alkenes, Alkynes, and Alkyl Halides.- D. Other Reactions.- 14: Phase-Transfer Catalysis in Analytical Chemistry.- A. The PTC/Analytical Chemistry Match.- B. Esterification, Etherification, and Other Nucleophilic Derivatizations.- C. Non-Nucleophilic PTC Reactions Used in Analytical Chemistry.- 15: Phase-Transfer Catalysis: Industrial Perspectives.- A. Industrial Background.- B. Evaluation of PTC as a Commercial Manufacturing Process Technology.