Organometallic Syntheses

ForewordPrefacePart I General Experimental Techniques in the Organometallic Chemistry of Nontransition Metals A. Establishment of Anhydrous and Anaerobic Reaction Media 1. General Reactivity Considerations for s-Bonded Organometallics 2. Inert Gases 3. Inert Solvents 4. Drying and Deoxygenating the Reaction Zone 5. Storage and Transfer of Organometallic Compounds B. Execution of Organometallic Reactions 1. Purity of Reagents 2. State of Subdivision 3. Solvent 4. Mode of Admixing 5. Temperature Control 6. Catalysts and Promoters 7. Precipitation and Filtration 8. Gas Evolution 9. Monitoring the Course of Reaction C. Purification of Organometallic Products 1. Consideration of Thermal and Light Instability 2. Complex Formation 3. Extraction 4. Chromatography 5. Recrystallization 6. Distillation D. Characterization of Organometallic Compounds 1. Physical Properties 2. Elemental Analysis 3. Molecular Weight 4. Hydrolysis and Other Carbon-Metal Bond Cleavages 5. Spectroscopy ?. Safety Measures 1. General Precautions 2. Toxicity Dangers 3. Fire Hazards 4. ExplosionsPart II Specific Preparations of Nontransition-Metal Organometallic Compounds A. Introduction 1. Criteria Governing the Choice of Procedures 2. General Procedural Observations B. Compounds of Group IA 1. General Preparative and Analytical Methods 2. Allyllithium 3. p-Bromophenyllithium 4. Benzyllithium 5. Phenoxymethyllithium 6. Diphenylmethyllithium 7. Triphenylmethyllithium 8. (E,E)-1,2,3,4-Tetraphenyl-1,3-butadien-1,4-ylidenedilithium C. Compounds of Group IIA 1. General Preparative and Analytical Methods 2. a-Deuteriovinylmagnesium Chloride 3. Allylmagnesium Bromide 4. Diallylmagnesium 5. 3-(1-Bromomagnesiooxy-1-cyclohexyl)-propylmagnesium Bromide 6. (E)-2-Phenyl-1-phenylsulfonylvinyllithium and (E)-2-Phenyl-1-phenylsulfonylvinylmagnesium Bromide D. Compounds of Group IIB 1. General Preparative and Analytical Methods 2. Ethylzinc Halide 3. Diethylzinc 4. Di-1-alkynylmercury 5. Bis(trimethylsily)mercury 6. Phenylmercuric Bromide 7. Diphenylmercury 8. Bis[(E)-stilbenyl]mercury and Bis[(Z)-stilbenyl]mercury E. Compounds of Group IIIA 1. General Preparative and Analytical Methods 2. 1-Methyl-4,5-dihydroborepin and 1-Chloro-4,5-dihydroborepin 3. Phenylborane-Triethylamine 4. Phenylboron Dibromide and Diphenylboron Bromide 5. 1-Phenylboracyclopentane 6. Triphenylborane 7. Diphenyl(phenylethynyl)borane-Pyridine 8. Pentaphenylborole 9. Heptaphenyl-7-borabicyclo[2.2.1]heptadiene 10. Heptaphenylborepin 11. Salts of the Bis(2,2'-biphenylene)borate Anion 12. Diisobutylaluminum Deuteride 13. Diisobutyl[(Z)-1-trimethylsilyl-2-phenylethenyl]aluminum 14. Diphenylaluminum Chloride and Phenylaluminum Dichloride 15. Triphenylaluminum 16. Diphenyl(phenylethynyl)aluminum 17. Tribenzylaluminum 18. Diethylgallium Chloride 19. Diethylgallium Ethoxide 20. Triethylgallium 21. Triisobutylgallium 22. Triphenylgallium 23. Tri-n-decylgallium 24. Diethylindium Chloride 25. Triethylindium 26. Triisobutylindium 27. Triphenylindium 28. Thallium(I) Cyclopentadienide 29. Diphenylthallium Halide 30. Triphenylthallium F. Compounds of Group IVA 1. General Preparative and Analytical Methods 2.