Topics in Organic Electrochemistry

Introduction, by Albert J. Fry and Wayne E. Britton...vii Chapter 1. The Electrochemistry of Nonbenzenoid Hydrocarbons, by Albert J. Fry 1. Introduction...1 2. Benzenoid Hydrocarbons...4 3. Annulenes...7 4. Homoaromaticity...23 5. Fused-Ring Hydrocarbons...25 Chapter 2. Electochemical Applications in Organic Chemistry, by Vernon D. Parker 1. Introduction...35 2. Chemical Reactions Coupled to Charge Transfer...37 3. Direct Electrochemical Methods...42 4. Indirect Electrochemical Methods...50 5. The "Reaction Order Approach"...56 6. Putting It All Together, Practical Examples...63 7. Concluding Remarks...76 Chapter 3. The Electrochemistry of Transition Metal Organometallic Compounds, by John C. Kotz 1. Electrochemistry of the Metallocenes...83 2. Other "Sandwich" Compounds of Pi Donor Ligands...109 3. The Binary Metal Carbonyls...117 4. Metal Carbonyl Derivatives...121 5. Electrochemically Induced Reactions...142 6. Concluding Remarks...166 Chapter 4. Organic Photoelectrochemistry, by Marye Anne Fox 1. Introduction...177 2. Principles of Photoelectrochemistry...185 3. Types of Photoassisted Redox Reactions...191 4. Organic Photelectrochemical Reactions...196 5. Conclusions...221 Chapter 5. Structural Effects in Organic Electrochemistry, by Wayne E. Britton 1. Electrochemistry of Cyclooctatetraene...227 2. Electrochemistry of Unusual Double Bonds...238 3. The Electrochemistry of Vicinal Dihalides...246 Chapter 6. The Electrochemistry of Transition Metal Organometallic Compounds, by Masamichi Fujihira 1. Introduction...255 2. Modification of the Electrode Phase (Region I)...259 3. Modification of Regions II and III...260 4. Modification of the Reaction Layer and the Diffusion Layer (Region IV)s...273 5. Modification of the Solution Phase (Regions II+III+IV+V)...278 6. Modified Electrodes for Organic Electrochemistry...280 Index...295