Preparative Polar Organometallic Chemistry

I. Reactivity of Polar Organometallic Intermediates.- 1 Introduction.- 2 Alkylation.- 3 Hydroxyalkylation with Epoxides.- 4 Hydroxyalkylation with Carbonyl Compounds.- 5 Formylation with Dimethylformamide.- 6 Carboxylation.- 7 Reaction of Organoalkali Compounds with Carbon Disulfide.- 8 Addition of Organoalkali Compounds to Isocyanates and Isothiocyanates.- 9 Sulfenylation.- 10 Trimethylsilylation.- 11 Reactions of Organometallic Compounds with Chloroformates and Dimethylcarbamoyl Chloride.- 12 Reactions of Organoalkali Compounds with Halogenating Agents.- 13 Conjugate Additions.- II. Metallation of Aromatic and Olefinic Hydrocarbons.- 1 Introduction.- 2 Metallation of Alkylbenzenes and Alkylnaphthalenes.- 3 Dimetallation of Aromatic Compounds.- 4 Metallation of Olefinic Compounds.- 5 Stereochemistry of Allylic Metallations.- 6 Dimetallation of Olefins.- 7 Experiments.- 8 Selected Procedures from Literature.- III. Metallation of Saturated Sulfur Compounds.- 1 Introduction.- 2 Substrates and Metallation Conditions.- 3 Experiments.- 4 Selected Procedures from Literature.- IV. ?-Metallation of Derivatives of Toluene Containing Heterosubstituents.- 1 Scope of this Chapter.- 2 Experiments.- V. Metallation of Heterosubstituted Allylic and Benzylic Compounds.- 1 Introduction.- 2 Substrates and Metallation Conditions.- 3 Experiments.- VI. Metallation of Heterocyclic Compounds.- 1 Introduction.- 2 Metallation of Alkyl Derivatives of Pyridine and Quinoline.- 3 Lateral Metallation of 2-Substituted Oxazolines, Thiazolines, Dihydrooxazines and Thiazoles.- 4 Experiments.- 5 Organic Syntheses Procedures.- VII. Metallation of Aldimines and Ketimines.- 1 Introduction.- 2 Conditions for the Metallation.- 3 Experiments.- 4 Organic Syntheses Procedures.- VIII. Metallation of Nitriles andIsonitriles.- 1 Introduction.- 2 ?-Metallation of Nitriles.- 3 Metallation of Isonitriles.- 4 Experiments.- IX. Generation of Lithium Halocarbenoids.- 1 Introduction.- 2 Methods of Generation of Lithium Halocarbenoids.- 3 Experimental Conditions and Techniques in Carbenoid Chemistry.- 4 Experiments.- X. Metallation of Carbonyl and Thiocarbonyl Compounds.- 1 Introduction.- 2 Mono Metallation of Carbonyl and Thiocarbonyl Compounds.- 3 Other Methods for the Generation of Enolates and Enethiolates.- 4 Dimetallation of Carbonyl and Thiocarbonyl Compounds.- 5 Experiments.- Metallation-Functionalization Index (Vol. 2).- Syntheses of Reagents and Starting Compounds (Vols. 1 and 2)..- Complementary Index (Vols. 1 and 2).- Typical Procedures and Special Techniques (Vols. 1 and 2).- Purification and Storage and Some Reagents and Solvents (Vols. 1 and 2).