Table of Contents

1. General Considerations.- 1. Introduction.- 1.1. Historical and General Description of Neighboring Group Effects.- 1.2. Terms and Definitions.- 2. Some Factors that Influence Anchimeric Assistance.- 2.1. The Stabilities of Bridged Carbocations—Some Molecular Orbital Calculations.- 2.2 Hyperconjugation—An Alternative Explanation?.- 2.3. The Effect of Intramolecularity—Ring Size and gew-Dialkyl Effects.- 2.3.1. Ring Size.- 2.3.2. The gem-Dialkyl Effect.- 3. Some Experimental Methods Used in the Study of Neighboring Group Participation.- 3.1. Kinetic Methods.- 3.1.1. Estimation of Reaction Rates.- 3.1.2. Participation as a Function of Electron Demand.- 3.1.3. Kinetic Isotope Effects.- 3.2. Investigation of Solvent Effects.- 3.3. Isolation or Trapping of Intermediates.- 3.4. Spectroscopic Observation of Intermediates.- 3.5. Product Analysis.- 2. Participation by Simple Oxygen, Sulfur, and Nitrogen Groups.- 4. Participation by Oxygen Groups.- 4.1. Ether Groups.- 4.1.1. In Solvolytic Displacement Reactions.- 4.1.2. In Reactions at Carbonyl Carbon.- 4.1.3. In Electrophilic Addition Reactions.- 4.2. Hydroxyl Groups.- 4.2.1. In Solvolytic Displacement Reactions.- 4.2.2. In Addition Reactions.- 4.2.3. In Elimination Reactions.- 4.2.4. In Hydrolysis and Related Reactions.- 4.2.5. In Reduction Reactions.- 4.3. Hydroperoxide Groups.- 4.4. Oxime Groups.- 5. Participation by Sulfur Groups.- 5.1. Thioether Groups.- 5.1.1. In Solvolytic Displacement Reactions.- 5.1.2. In Electrophilic Addition Reactions.- 5.1.3. In Elimination Reactions.- 5.1.4. In Free-radical, Carbene, and Phohemical Reactions.- 5.2. Thiol Groups.- 6. Participation by Nitrogen Groups.- 6.1. Amino Groups.- 6.1.1. Anchimeric Assistance in Ring Closure Reactions.- 6.1.2. R2N-3 Participation.- 6.1.3. R2N-4 Participation.- 6.1.4. R2N-5 and R2N-6 Participation.- 6.1.5. Miscellaneous Modes of Participation.- 6.2. Nitrile Groups.- 6.3. Hydrazone Groups.- Author Index.