The Anomeric Effect and Related Stereoelectronic Effects at Oxygen

A. Stereoelectronic Effects on Structure.- 1. Introduction.- 2. The Anomeric Effect.- 3. The Reverse Anomeric Effect.- 4. The Exo-Anomeric Effect.- 5. The Generalised Anomeric Effect.- 6. The Gauche Effect.- B. The Electronic Basis of the Effects.- 1. Introduction.- 2. The Status of Lone Pair Electrons.- 3. Calculations on X?Y Systems.- 4. Effects on Bond Lengths and Angles.- 5. Effects in Furanoses.- 6. The Stereoelectronic Basis of the Anomeric Effect.- 7. Related Stereoelectronic Effects.- C. Stereoelectronic Effects on Reactivity: The Kinetic Anomeric Effect.- 1. Introduction.- 2. Reactions of the Acetal Group.- 3. The Hydrolysis of Orthoesters.- 4. Carbonyl-Oxygen Exchange Reactions of Esters and Amides.- 5. The Hydrolysis of Imidate Esters: Stereoelectronic Effects at Oxygen and Nitrogen.- 6. Reactions of Phosphate Esters.- 7. Radical Reactions.- 8. Enzyme Reactions.- D. Appendix.- 1. Canonical Lone Pair Description.- 2. Hybrid Lone Pair Description.- E. References.- F. Subject Index.