Phase-Transfer Catalysis: Fundamentals, Applications, and Industrial Perspectives (1994)

Preface. Part 1: Basic concepts in phase-transfer catalysis: Phase-transfer-catalyzed reactions Basic steps of phase-transfer catalysis The PTC reaction rate matrix Anion transfer and anion activation Effect of reaction variables on transfer and intrinsic rates Outline of compounds used as phase-transfer catalysts. Part 2: Phase-transfer catalysts -- Fundamentals I: Introduction Structural factors affecting the distribution of anions between aqueous and organic phases Structural factors affecting the distribution of phase-transfer catalyst cations between the aqueous and organic phases Effects of the organic phase polarity on the distribution of phase-transfer cation-anion pairs Effects of changes in organic phase polarity during reaction Factors affecting the distribution of phase-transfer catalyst cation-anion pairs between an organic phase and an aqueous phase containing hydroxide ion Effect of hydration of the transferred anion and the effect of inorganic salt and/or hydroxide concentration in the aqueous phase. Part 3: Phase-transfer catalysis -- Fundamentals II: Introduction Liquid-liquid PTC Solid-liquid PTC. Part 4: Phase-transfer catalysts: Introduction Use of quaternary salts as phase-transfer catalysts Macrocyclic and macrobicyclic ligands PEGs, Tris (3, 6-dioxahepty)amine (TDA-1), and related ethoxylated compounds as phase-transfer catalysts Other soluable polymers and related multifunctional compounds as phase-transfer catalysts Use of dual PTC catalysts or use of cocatalysts in phase-transfer systems Catalysts for transfer of species other than anions Separation and recovery of phase-transfer catalysts. Part 5: Insoluable phase-transfer catalysts: Introduction PTC catalysts bound to insoluable resins Phase-transfer catalysts bound to inorganic solid supports PTC catalysts contained in a separate liquid phase (Third-liquid-phase catalyst). Part 6: Variables in reaction design for laboratory and industrial applications of phase-transfer catalysis: Choice of catalyst Choice of solvent Presence of water Agitation Choice of anion, leaving group, and counteranion Choice of base Guidelines for exploring new PTC applications. Part 7: Phase-transfer catalysis displacement reactions with simple anions: General considerations Behavior of various anions in PTC displacement reactions. Part 8: Phase-transfer catalysis reaction with strong bases: C-Alkylation N-Alkylation O-Alkylation -- Etherification S-Alikylation -- Thioetherification Dehydrohalogenation Carbene reactions Condensation reactions Deuterium exchange, isomerization, and oxidation. Part 9: Phase-transfer catalysis -- Polymerization and polymer modification: Introduction Polymer synthesis Chemical modification of polymers. Part 10: Phase-transfer-catalyzed oxidations: Introduction Permanganate oxidations Oxidations with hyperchlorite and hypobromite PTC oxidations with hydrogen peroxide PTC air or oxygen oxidations Oxidations by persulfates PTC oxidations with nitric acid PTC carbon tetrachloride/sodium hydroxide oxidations PTC oxidations with perborate PTC oxidations with ferrate and ferricyanide PTC oxidations with superoxide PTC electrochemical oxidations PTC oxidations with other oxidents. Part 11: Phase-transfer-catalyzed reductions: Sodium borohydride reductions Lithium aluminum hydride reductions Reductions with sodium formate Reductions with sulfur-containing anions Hydrogenation Reductions with formaldehyde Electrochemical reduction Photochemical reduction Wolff-Kishner reduction Reduction by dodecarbonyltriiron and related species. Part 12: Phase-transfer catalysis -- Chiral phase-transfer catalyzed formation of carbon-carbon bonds: Introduction Alkylation reactions. Part 13: Phase-transfer catalysis - Transition metal cocatalyzed reactions: Introduction Carbonylation and reactions with carbon monoxide PTC reduction and hydrogenation