Di- and Polyalkali Metal Derivatives of Heterofunctionally Substituted Organic Molecules

Treatment of a wide variety of organic molecules with two or more molar equivalents of strongly basic alkali metal reagents affords di- or polyalkali metal derivatives which readily condense with electrophilic reagents to afford synthetically useful compounds. This review describes the preparation and subsequent chemistry of such multiple metal compounds derived from mono-, di-, and polyketones, ß-ketoesters, ylides, carboxylic acids, carboxamides, imides, sulfonamides, sulfones, sulfoxides, nitriles, oximes, hydrazones, azines, alcohols, thiols, ethers, amines, and certain sulfur-containing heterocyclic compounds. 1. Introduction 2. Diketones, Ketoaldehydes, and Related Compounds 2.1. Alkylation Reactions 2.2. Condensation Reactions with Aldehydes and Ketones 2.3. Aroylation and Acylation Reactions 2.4. Other Addition Reactions 3. ß-Ketoesters 4. Metalation of Ylides 5. Carboxylic Acids 6. Carboxamides 7. Imides 8. Sulfonamides 9. Sulfones and Sulfoxides 10. Nitriles 11. Oximes, Hydrazones, and Azines 12. Alcohols, Thiols, Ethers, and Sulfides 13. Amines 14. Miscellaneous Heterocyclic Compounds 15. Addenda