Activated Metals in Organic Synthesis

PART ONE: METAL ACTIVATION, I. BASIC FORMS OF METALS, A. MASSIVE METALS, B. DISPERSED METALS, 1. Metal Films, 2. Metal Powders, 3. Organometallic Powders, 4. Other Dispersed Forms, II. METAL VAPOR CHEMISTRY, A. GENERAL CONSIDERATIONS, B. ALKALI AND ALKALINE-EARTH METAL VAPORS, C. TRANSITION METAL VAPORS, D. METAL ATOM-SOLVENT CONDENSATIONS, E. OTHER APPLICATIONS, III. DEPASSIVATING METHODS, A. ACTIVATION BY REAGENTS AND SOLVENTS, B. RIEKE METALS, C. METAL ANTHRACENE/NAPHTHALENIDE, D. OTHER REDUCING METHODS, E. INTERMETALLIC COUPLES, F. ULTRASONIC IRRADIATION, 1. Sonochemistry. Basic Principles, 2. Reactions on Metal Surfaces, 3. Reactive Metal Powders, 4. Organometallic Compounds, G. METAL GRAPHITES, 1. Introduction, 2. Structural Considerations, 3. Graphite Intercalation Compounds, 4. Metal Dispersions on Graphite Surfaces, 5. Other Metallic Graphite Compounds, PART TWO: METAL-MEDIATED REACTIONS IV. REDUCTIONS, A. UNSATURATED SYSTEMS, 1. Alkenes, Alkynes, and Aromatic Systems, 2. Carbonyl Substrates, 3. Conjugated Reduction, B. ORGANIC HALIDES AND RELATED SYSTEMS, C. DEOXYGENATION REACTIONS, D. REDUCTION OF NITROGEN AND SULFUR, FUNCTIONAL GROUPS, REDUCTIVE CARBONYL COUPLING REACTIONS, A. PINACOL REACTION, 1. Classical Methods, 2. Low-Valent Metal Reagents, 3. Other Metal-mediated Pinacolic Reactions, B. McMURRY-TYPE REACTIONS, 1. Titanium Reagents, 2. Scope and Limitations, 3. McMurry Coupling with Metals other than Titanium, VI. ADDITION REACTIONS TO CARBONYL COMPOUNDS, A. BARBIER-TYPE REACTIONS, 1. Introduction, 2. Activated Metals, 3. Reactions in Aqueous Media, B. REFORMATSKY-TYPE REACTIONS, 1. Introduction, 2. The Reformatsky Reagent, 3. The Role of Zinc Activation, 4. Metals other than Zinc, 5. Stereoselective Reformatsky Reactions, VII. CYCLIZATIONS, A. SIMMONS-SMITH-TYPE REACTIONS, 1. Introduction, 2. Simmons-Smith Reagents, 3. Metals other than Zinc, B. CYCLOADDITIONS, C. REFORMATSKY-TYPE CYCLIZATIONS, 1. Dreiding-Schmidt Reactions, 2. Intramolecular Reactions, 3. Other Zinc-mediated Cyclizations, D. MISCELLANEOUS CYCLIZATIONS, VIII. THE BERNET-VASELLA REACTION, A. INTRODUCTION, B. ZINC REAGENTS, C. SYNTHETIC APPLICATIONS, Index